Maryland vacation rentals you can book direct

Maryland rentals at a glance

Counted from what hosts list. Check the listing before you book.

Homes in Maryland for 6 or more

8 of the 653. Search them with your dates →

The Jolly Roger

Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is open to guests and offers many water sporting opportunities during your stay! Nestled in the desirable quiet Arden on the Severn community.

📍 Arden on the Severn, MD

👥 8

$743 / night

excl. host's fees

Chesapeake Waterfront - 7BR,5BA - Beach, Pool, Dock

Private, 6 acre property w/ waterfront, sandy beach, pool, tidal pond, dock, decks, boats, bikes, games & more. Beautiful, newer custom 3-story home w/ wrap-around porches, Families & groups LOVE our 7 Bedroom, 5 Bath luxury property The 3rd floor is a haven for kids with a game room, two bdrms & a bath.

📍 Woolford, MD

👥 18🛏️ 7🚿 5

$813 / night

Union House

Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly restored with attention to detail, this light-filled home will welcome you back in time with historic features like the double-sided (decorative) brick fireplace, 9’ ceilings and hardwoods floors, while…

📍 Annapolis, MD

👥 6🛏️ 3🚿 2

~$634 / night

estimate

Pickleball, Blackstone & Pond: 2.5 hrs from DC

Welcome to the spacious 5BR 2.5BA farmhouse on a secluded 75-acre property near Manchester, MD, in scenic Carroll County. It promises a relaxing retreat near the state line, exciting local attractions, and natural landmarks. The unique design, beautiful surroundings, and a rich amenity list will leave you in awe.

📍 Manchester, MD

👥 16🛏️ 5🚿 2.5

~$433 / night

estimate

All Decked Out in Annapolis

Welcome to All Decked Out, your dream escape in the waterfront Oyster Harbor Community of Annapolis, a tranquil retreat on the Annapolis Neck Peninsula. This beautifully renovated 4-bedroom, 3-bath home blends modern elegance with timeless coastal charm.

📍 Annapolis, MD

👥 12

$100 / night

excl. host's fees

Cozy on Cornhill

In the shade of the Maryland Statehouse, this historic home has welcomed family, friends, and travelers for more than 175 years. Tucked on a quiet side street in the heart of Annapolis, the property blends timeless character with modern comfort—offering an ideal stay for guests who want both history and convenience.

📍 Annapolis, MD

👥 8

$100 / night

excl. host's fees

Waterfront! Private Dock, Boat Tie-Up & Near Town

Unwind with family or friends at this perfect waterfront getaway. This spacious home features a large sunroom with beautiful water views, ideal for watching the activity on the water. It sleeps up to 12 guests and is accessible by car or boat, with a private dock for tying up.

📍 Rock Hall, MD

👥 12🛏️ 5🚿 3

$276 / night

Happy Hours

Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior.

📍 Annapolis, MD

👥 8🚿 2

$491 / night

excl. host's fees

Homes in Maryland with a pool

8 of the 386. Search them with your dates →

Chesapeake Waterfront - 7BR,5BA - Beach, Pool, Dock

Private, 6 acre property w/ waterfront, sandy beach, pool, tidal pond, dock, decks, boats, bikes, games & more. Beautiful, newer custom 3-story home w/ wrap-around porches, Families & groups LOVE our 7 Bedroom, 5 Bath luxury property The 3rd floor is a haven for kids with a game room, two bdrms & a bath.

📍 Woolford, MD

👥 18🛏️ 7🚿 5

$813 / night

Lazy Creek - Deep Creek Lake - Indoor Lazy River , Boat Dock rental available May-Sept. 2026

Lazy Creek is a one-of-a-kind signature home at Deep Creek Lake — the first and only property in Deep Creek with its own private indoor lazy river. Float year-round in complete privacy, then jump in the indoor pool, unwind in the hot tub, or settle into the home theater with surround sound.

📍 Deep Creek, MD

👥 20🛏️ 8🚿 9

$1,026 / night

Sunset Island -5BR, Sleeps 12/ indoor outdoor pool

Tucked along Assawoman Bay in Ocean City’s private Sunset Island community, this stunning 4-story, 5-bedroom townhouse is your perfect vacation retreat. Just steps from the clubhouse and amenities, it sleeps 12 with 3 full baths and 1 half bath for ideal comfort and privacy.

📍 Ocean City, MD

👥 12🛏️ 5🚿 4

$562 / night

67th Ocean Block 4 BR Townhouse Sleeps 12, Pool

Escape to this stunning oceanfront townhouse on 67th Street in Ocean City, Maryland, perfect for a family getaway! With four floors of living space and breathtaking Atlantic Ocean views, this property offers four bedrooms and five decks for ultimate relaxation.

📍 Ocean City, MD

👥 12🛏️ 4🚿 3

$515 / night

Licking Creek Retreat

4BR, 4BA, Amazing Indoor Pool, EV charger, next to Camp Harding and Fishing Creek. Unplug & Unwind!. Enjoy a private retreat on almost 10 acres within driving distance from DC, VA and MD with indoor heated salt water pool. Theatre room with reclining seats. Walk to Camp Harding Park with many park amenities.

📍 Big Pool, MD

👥 10🛏️ 4🚿 4

~$600 / night

estimate

Oceanfront Corner Condo with Pool

Stunning renovated 2-bed/2-bath beachfront corner condo with panoramic ocean & bay views from a wrap-around balcony. Bright, open-concept living space perfect for families. Enjoy the building pool and walk to the boardwalk, Jolly Rogers Amusement Park, and local dining. Park your car and explore everything on foot!

📍 Ocean City, MD

👥 8🛏️ 2🚿 2

$297 / night

Oceanfront Penthouse w/ Wraparound Balcony & Pools

Unique oceanfront penthouse in the popular Sea Watch building that offers the best amenity package in Ocean City, Maryland. This condo’s unique layout affords the entire living area and every bedroom in the condo direct ocean views.

📍 Ocean City, MD

👥 10🛏️ 2🚿 2.5

$323 / night

5 Corner Store Ln Sunset Island | Resort Community

10% off July and August pricing! ✹ Mandatory Sunset Island Resort Fee: $200 Summer 2025 (May 25 – Sept 6) — paid directly to management at or before check-in. These are 2026 rates and 2027 rates are TBD and may increase ✹ ✹ Must be 25+ to rent and stay - no graduating HS groups.

📍 Ocean City, MD

👥 12🛏️ 5🚿 4

$338 / night

Homes in Maryland

Homes with the host's own booking site first. Prices can change and may not be exact; the asterisk shows what each one includes.

The Jolly Roger

Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is open to guests and offers many water sporting opportunities during your stay! Nestled in the desirable quiet Arden on the Severn community.

📍 Arden on the Severn, MD

👥 8

$743 / night

excl. host's fees

Chesapeake Waterfront - 7BR,5BA - Beach, Pool, Dock

Private, 6 acre property w/ waterfront, sandy beach, pool, tidal pond, dock, decks, boats, bikes, games & more. Beautiful, newer custom 3-story home w/ wrap-around porches, Families & groups LOVE our 7 Bedroom, 5 Bath luxury property The 3rd floor is a haven for kids with a game room, two bdrms & a bath.

📍 Woolford, MD

👥 18🛏️ 7🚿 5

$813 / night

Union House

Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly restored with attention to detail, this light-filled home will welcome you back in time with historic features like the double-sided (decorative) brick fireplace, 9’ ceilings and hardwoods floors, while…

📍 Annapolis, MD

👥 6🛏️ 3🚿 2

~$634 / night

estimate

Pickleball, Blackstone & Pond: 2.5 hrs from DC

Welcome to the spacious 5BR 2.5BA farmhouse on a secluded 75-acre property near Manchester, MD, in scenic Carroll County. It promises a relaxing retreat near the state line, exciting local attractions, and natural landmarks. The unique design, beautiful surroundings, and a rich amenity list will leave you in awe.

📍 Manchester, MD

👥 16🛏️ 5🚿 2.5

~$433 / night

estimate

Waterfront Retreat w Private Beach, Dock and Boat Lift

Escape to a private waterfront retreat in Princess Anne with a 100-foot pier and your own sandy beach. This 7-bedroom chateau-style getaway is perfect for families, reunions, and group trips, sleeping guests comfortably with 1 king, 4 queens, and 5 twins.

📍 Princess Anne, MD

👥 15🛏️ 7🚿 4

$630 / night

excl. host's fees

All Decked Out in Annapolis

Welcome to All Decked Out, your dream escape in the waterfront Oyster Harbor Community of Annapolis, a tranquil retreat on the Annapolis Neck Peninsula. This beautifully renovated 4-bedroom, 3-bath home blends modern elegance with timeless coastal charm.

📍 Annapolis, MD

👥 12

$100 / night

excl. host's fees

Cozy on Cornhill

In the shade of the Maryland Statehouse, this historic home has welcomed family, friends, and travelers for more than 175 years. Tucked on a quiet side street in the heart of Annapolis, the property blends timeless character with modern comfort—offering an ideal stay for guests who want both history and convenience.

📍 Annapolis, MD

👥 8

$100 / night

excl. host's fees

Waterfront! Private Dock, Boat Tie-Up & Near Town

Unwind with family or friends at this perfect waterfront getaway. This spacious home features a large sunroom with beautiful water views, ideal for watching the activity on the water. It sleeps up to 12 guests and is accessible by car or boat, with a private dock for tying up.

📍 Rock Hall, MD

👥 12🛏️ 5🚿 3

$276 / night

Cool Spring Cove

Welcome to this beautiful waterfront home in the quiet Cool Spring Cove of the Magothy River in Arnold, MD. Not only does this home have beautiful views, but it also has a pool and pier. Enjoy your morning beverage on the private deck overlooking the pool and water views.

📍 Cherrywood, MD

👥 4🛏️ 4🚿 1

~$662 / night

estimate

Happy Hours

Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior.

📍 Annapolis, MD

👥 8🚿 2

$491 / night

excl. host's fees

Phillip Clayton House

Historic Philip Clayton House – Downtown Annapolis Retreat Step into Annapolis history at the Philip Clayton House, a landmark residence built in 1834. Located just one block from the City Dock, 3 blocks from the U.S.

📍 Annapolis, MD

👥 10🚿 5

$100 / night

excl. host's fees

Around the Corner

Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly named "Around the Corner" for its prime location near Annapolis' best dining, shopping, and waterfront experiences.

📍 Annapolis, MD

👥 8

$529 / night

excl. host's fees

Oh Happy Bay

Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Bembe Beach with direct access to safe, shallow water for swimming, paddle boarding, and boating (small boat mooring).

📍 Annapolis, MD

👥 8🛏️ 2

~$180 / night

estimate

Lazy Creek - Deep Creek Lake - Indoor Lazy River , Boat Dock rental available May-Sept. 2026

Lazy Creek is a one-of-a-kind signature home at Deep Creek Lake — the first and only property in Deep Creek with its own private indoor lazy river. Float year-round in complete privacy, then jump in the indoor pool, unwind in the hot tub, or settle into the home theater with surround sound.

📍 Deep Creek, MD

👥 20🛏️ 8🚿 9

$1,026 / night

The Annapolis Firehouse

This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in 1864, Eastport native Art Tuers joined the company in 1949 at the age of 16.

📍 Annapolis, MD

👥 8

$547 / night

excl. host's fees

The Randall House

The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The Randall House, with its 4 bedroom and 4 Baths, is located just steps from the USNA Gate 1, downtown shops, restaurants & City Dock.

📍 Annapolis, MD

👥 11🛏️ 4🚿 4

~$600 / night

estimate

The Wisteria

How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the Annapolis waterfront, the State Capitol, restaurants, shopping and the Naval Academy, this cherished property is registered with the Historical Society of Annapolis (originally home to “Sam’s Grocer…

📍 Annapolis, MD

👥 7🛏️ 4🚿 4

~$843 / night

estimate

Cedar House on East

Step into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this property is recognized in the Historic District’s National Registry as one that “embodies the distinctive characteristics of a period.” Over the centuries, it has served as a shoemaker’s store, an inn,…

📍 Annapolis, MD

👥 8🛏️ 3

~$590 / night

estimate

Bay Cottage

Relaxing Waterfront Retreat Near Annapolis – Pet Friendly & Packed with Perks! Escape to a tranquil waterfront retreat with stunning views of the Chesapeake Bay and Bridge!

📍 Annapolis, MD

👥 8

$501 / night

excl. host's fees

Washington's Retreat

Family Rental only! This brand new custom home was built with stunning views of the Chesapeake Bay and all the bells and whistles, including a large private pool (open late April-end of Oct), hot tub (available year round) and game room on a semi-private beach.

📍 Deale, MD

👥 8

$888 / night

excl. host's fees

Song of River City

Escape to this charming riverfront home, just one mile from the heart of Edgewater and 15 minutes from downtown Annapolis. This family-friendly getaway offers the perfect balance of relaxation and adventure, with a private dock, spacious backyard, and stunning water views.

📍 Londontowne, MD

👥 10🛏️ 6

$501 / night

excl. host's fees

Gatehouse Annapolis

Historic Charm Across from the Naval Academy Nestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-bath historic brick row home is a rare gem. Located directly across from the U.S.

📍 Naval Academy, MD

👥 10

$500 / night

excl. host's fees

Haiku River House

A tranquil Japanese-inspired riverfront estate just 18 minutes from Downtown DC. This stunning 5BR/4BA single-level home sleeps 10 guests in curated comfort — featuring Potomac River views, a chef's kitchen, Peloton bike, Golden Tee arcade, designer mattresses, Smart TVs in every room, and private en-suite baths thr…

📍 Fort Washington, MD

👥 10🛏️ 5🚿 5

~$653 / night

estimate

River Breeze

1BR 1 bath in Severna Park

📍 Severna Park, MD

👥 12🛏️ 1🚿 1

~$629 / night

estimate

400 of the 796 homes in Maryland

• The Jolly Roger · sleeps 8
• Chesapeake Waterfront - 7BR,5BA - Beach, Pool, Dock · 7 bd · sleeps 18
• Union House · 3 bd · sleeps 6
• Pickleball, Blackstone & Pond: 2.5 hrs from DC · 5 bd · sleeps 16
• Waterfront Retreat w Private Beach, Dock and Boat Lift · 7 bd · sleeps 15
• All Decked Out in Annapolis · sleeps 12
• Cozy on Cornhill · sleeps 8
• Waterfront! Private Dock, Boat Tie-Up & Near Town · 5 bd · sleeps 12
• Cool Spring Cove · 4 bd · sleeps 4
• Happy Hours · sleeps 8
• Phillip Clayton House · sleeps 10
• Around the Corner · sleeps 8
• Oh Happy Bay · 2 bd · sleeps 8
• Lazy Creek - Deep Creek Lake - Indoor Lazy River , Boat Dock rental available May-Sept. 2026 · 8 bd · sleeps 20
• The Annapolis Firehouse · sleeps 8
• The Randall House · 4 bd · sleeps 11
• The Wisteria · 4 bd · sleeps 7
• Cedar House on East · 3 bd · sleeps 8
• Bay Cottage · sleeps 8
• Washington's Retreat · sleeps 8
• Song of River City · 6 bd · sleeps 10
• Gatehouse Annapolis · sleeps 10
• Haiku River House · 5 bd · sleeps 10
• River Breeze · 1 bd · sleeps 12
• Green on Fleet · sleeps 4
• River Cottage · sleeps 2
• River Breeze Estate - Commissioning Week Only · 4 bd · sleeps 12
• Anchor House | Pier, Boat Dock, & Gazebo Luxe Home · 4 bd · sleeps 11
• On The Waterfront · 6 bd · sleeps 12
• Sunset Island -5BR, Sleeps 12/ indoor outdoor pool · 5 bd · sleeps 12
• The Log House at Sugarloaf Mountain MD · 5 bd · sleeps 17
• Sunset Serenity · 5 bd · sleeps 10
• The Crooked Oak Lodge - Deep Creek Lake - Indoor Pool & Hot Tub · 8 bd · sleeps 20
• Sunset Island Townhouse - 5 Bdr/ Sleeps 12/ pool · 5 bd · sleeps 12
• 2BR Bungalow -patio space-dog friendly- sleeps 4 · 2 bd · sleeps 4
• Kentmorr Pool Cottage · 3 bd · sleeps 11
• 67th Ocean Block 4 BR Townhouse Sleeps 12, Pool · 4 bd · sleeps 12
• Licking Creek Retreat · 4 bd · sleeps 10
• Oceanfront Corner Condo with Pool · 2 bd · sleeps 8
• Oceanfront Penthouse w/ Wraparound Balcony & Pools · 2 bd · sleeps 10
• 5 Corner Store Ln Sunset Island | Resort Community · 5 bd · sleeps 12
• Pet-Friendly Downtown Beach Bungalow · 4 bd · sleeps 8
• Roost on the River · 3 bd · sleeps 6
• Adagio 302 · 3 bd · sleeps 8
• Direct Oceanfront Condo · 2 bd · sleeps 6
• Grays Inn Creek Waterfront Pvt Dock Kayaks & View · 7 bd · sleeps 18
• Entire 10BR House Steps to Beach · 10 bd · sleeps 30
• Oceanfront 1BR Condo with a Pool · 1 bd · sleeps 4
• Oceanfront Living at Its Finest in Ocean City, MD · 3 bd · sleeps 10
• Parrot Bay Townhouse 27 | Pet Friendly · 3 bd · sleeps 10
• Windjammer Beach House · 4 bd · sleeps 9
• Rooftop Pool Condo Steps from Ocean City Beach · 3 bd · sleeps 9
• Oceanfront Condo w/ Indoor Pool & Beach Access · 2 bd · sleeps 6
• Lighthouse Dual Townhomes Steps to the Beach · 6 bd · sleeps 24
• Beachwalk 20, Steps to the Beach, Outdoor Pool · 4 bd · sleeps 10
• Oceanside Condo by the Beach · 2 bd · sleeps 6
• Golden Sands 701, Beachfront Family Resort Escape · 3 bd · sleeps 8
• Waterfront Home w/ Rooftop Deck & Pet-Friendly · 3 bd · sleeps 9
• Beautifully Renovated Two Bedroom Oceanfront Condo · 2 bd · sleeps 8
• Direct Oceanfront Condo with Indoor Pool · 1 bd · sleeps 4
• Hook, Wine, & Sinker | Bay Views + Boat Dock · 4 bd · sleeps 8
• Island Cabana 204 · 3 bd · sleeps 10
• The Chesapeake House · 6 bd · sleeps 16
• Direct Oceanfront Condo w/ Balcony & Pool Access · 2 bd · sleeps 8
• 6 Corner Store Ln · 5 bd · sleeps 12
• 5BR Oceanview Home Private Pool · 5 bd · sleeps 18
• New Townhome Steps from the Beach · 3 bd · sleeps 10
• Oceanfront Condo w/ Balcony & Free Parking · 2 bd · sleeps 8
• Diamond Beach 108 · 1 bd · sleeps 6
• Stunning Top-Floor Oceanfront Condo · 1 bd · sleeps 4
• 144 East 104 · 2 bd · sleeps 6
• One Bedroom Direct Oceanfront Condo with Pool · 1 bd · sleeps 4
• Vagabond Penthouse | Ocean Views + Huge Deck · 5 bd · sleeps 10
• SSI 44 Sunset ISL Dr · 5 bd · sleeps 12
• Ocean Pines Chalet · 4 bd · sleeps 10
• Ocean Place 402 | Oceanfront Balcony Views · 2 bd · sleeps 6
• Bayfront Paradise, Pool, Boat Slip, Townhome · 2 bd · sleeps 8
• Large Direct Bayfront Home with Great Amenities · 5 bd · sleeps 9
• West Winds 304 · 1 bd · sleeps 6
• Z Estates | Balcony Beach View Townhome + Pool · 3 bd · sleeps 11
• Waterfront Retreat with Boat Dock · 3 bd · sleeps 7
• Harbour Sails 5 · 3 bd · sleeps 10
• Downtown Villa Steps to the Beach · 4 bd · sleeps 14
• Bayview Condo Short Walk to Beach · 2 bd · sleeps 4
• Beachcomber · sleeps 6
• Canal Front Golf Retreat w/Dock · 3 bd · sleeps 6
• Ocean Pines 6BR Canal Front Home · 6 bd · sleeps 16
• Bayside Townhome with Sunset Views · 3 bd · sleeps 10
• Spacious Group Retreat Steps to Beach · 6 bd · sleeps 16
• Bayside Bliss | 5 Min to Beach · 3 bd · sleeps 6
• Bayview Grand 102 (check out incentives) · 4 bd · sleeps 12
• Four Bedroom Waterfront Condo with Great Location · 4 bd · sleeps 8
• The Salty St. Louis · 4 bd · sleeps 10
• Wisp'd Away-Lakefront*DOCK*on 3+acres · 4 bd · sleeps 12
• Spacious House Steps to the Beach · 4 bd · sleeps 13
• Downtown OC Townhome! (A) · 3 bd · sleeps 13
• Downtown OC Dual Townhomes | Large Groups + Steps to the Beach · 6 bd · sleeps 26
• Waterfront 4BR Home with Pier & Views · 4 bd · sleeps 10
• Surf Crest 205 · 2 bd · sleeps 6
• Waterfront Getaway with Boat Slip · 2 bd · sleeps 6
• All Tucked Inn · 2 bd · sleeps 6
• Riverfront Hangar · sleeps 12
• Soothing Shores · sleeps 6
• The Yard · 5 bd · sleeps 12
• Historic Hideaway · sleeps 8
• Anchor at Annapolis Inn · sleeps 11
• Chesapeake Charmer · 4 bd · sleeps 8
• ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️ · 4 bd · sleeps 14
• Crew's Quarters · sleeps 6
• The Goat Locker · sleeps 11
• The Fleet's Inn · sleeps 4
• Cove Ct · 4 bd · sleeps 7
• Capital View · sleeps 8
• Lighthouse Inn · sleeps 12
• Thomas Hyde House · 6 bd · sleeps 12
• Blue Crab on Conduit · 3 bd · sleeps 7
• Manklin Creek Retreat | Water Views + Boat Dock · 3 bd · sleeps 6
• Rusty Anchor · 3 bd · sleeps 8
• The Pearl (of Oyster Harbor) · sleeps 8
• Maritime Manor · 6 bd · sleeps 13
• The Buccaneer · sleeps 8
• Stunner on the Severn · 4 bd · sleeps 10
• Leave of Absence · sleeps 3
• Magnolia Retreat on Charles · 3 bd · sleeps 6
• Settle Inn · 3 bd · sleeps 9
• Glen Riddle 102 · 4 bd · sleeps 12
• Westside Storied · sleeps 9
• Liberty Lookout · sleeps 7
• Blue Barn · 6 bd · sleeps 15
• Liberty Call · 4 bd · sleeps 9
• First Mate · sleeps 6
• Pinecrest Bungalow · sleeps 7
• Bayside Tiki · 3 bd · sleeps 8
• Sun village 3 · 3 bd · sleeps 11
• North Park · 3 bd · sleeps 6
• Hanover House · 4 bd · sleeps 8
• Catch 22 · 3 bd · sleeps 2
• Two Bedroom Beachfront End Unit Condo with Pool. · 2 bd · sleeps 8
• Bayfront Townhome with Amazing Views · 3 bd · sleeps 6
• Oceanfront 2BR Condo | Steps to Beach | Sleeps 8 · 2 bd · sleeps 8
• Chapel Vista · 2 bd · sleeps 7
• Ocean View Oasis: Steps to Beach, Sleeps 10 · 3 bd · sleeps 10
• Rustic Charm Meets Modern Boutique + DCL Central + Hot Tub, Sauna, Lake Access · 3 bd · sleeps 6
• Golden Sands 1412, Oceanfront, Pools, Games · 2 bd · sleeps 10
• Cottage · 3 bd · sleeps 8
• Golden Sands 1106: Gorgeous Oceanfront 1 BDRM condo, fully renovated and professionally decorated. All the comforts of home · 1 bd · sleeps 4
• Red Door Gem · 5 bd · sleeps 10
• Quay 2008 · 3 bd · sleeps 10
• 8240 Wilmington Ln | Family Townhome | Steps to the Beach · 4 bd · sleeps 10
• Isabella 4 | Ocean Block + Boardwalk · 3 bd · sleeps 12
• Blue Tides Family Retreat · 3 bd · sleeps 12
• Two Bedroom Beachfront Condo with Outdoor Pool · 2 bd · sleeps 8
• The Cove at Ocean Pines | Boater’s Paradise · 5 bd · sleeps 12
• Salty Sands 2 101 · 3 bd · sleeps 10
• Dolphins Chance - Waterfront Ocean Pines + Dock · 4 bd · sleeps 10
• Resort Condo with Pools by Beach · 3 bd · sleeps 8
• Robin’s Nest at Summer Winds · 2 bd · sleeps 6
• Oceanfront Condo w/Balcony & Easy Beach Access · 2 bd · sleeps 8
• Ocean Pines 2BR 1BA Cottage with Fire Pit · 2 bd · sleeps 6
• Parrot Bay 25 | Pet Friendly · 2 bd · sleeps 7
• Harbor Haven by the Boardwalk · 2 bd · sleeps 6
• Sunset Shores at Dune Mist · 3 bd · sleeps 7
• Canalfront Oasis | Boat Dock · 3 bd · sleeps 6
• Barefoot Country 1BR 1.5BA Ocean Front Condo · 1 bd · sleeps 4
• Direct Oceanfront Condo with the Best Amenities · 2 bd · sleeps 10
• The Treetop | Rooftop Deck & Screened Porch · 3 bd · sleeps 8
• The Salty Anchor Retreat · 3 bd · sleeps 8
• Buddy Beach | Ocean Views + Indoor Pool · 3 bd · sleeps 8
• Beach Place North 2 · 4 bd · sleeps 10
• Large Three Bedroom Oceanfront Condo with Pool · 3 bd · sleeps 8
• Renovated Three Bedroom Direct Bayfront Townhome · 3 bd · sleeps 7
• Coastal Marsh · 4 bd · sleeps 5
• Clammers Cove 4 · 4 bd · sleeps 10
• Nantucket 6 · 3 bd · sleeps 9
• Cinnamon Teal 4 · 3 bd · sleeps 8
• San Remo 108B · 2 bd · sleeps 10
• Broad Marsh Beach Home | Pool + Balcony Views · 5 bd · sleeps 14
• North, OC, 3B/3B, 1 Block to Beach + Linens · 3 bd · sleeps 10
• Ocean Hideaway 302 - Beachfront Condo · 2 bd · sleeps 8
• One Bedroom Oceanfront Condo with Outdoor Pool · 1 bd · sleeps 4
• Waterfront Getaway with Boat Slip · 3 bd · sleeps 8
• Downtown OC Townhome! - (B) · 3 bd · sleeps 13
• Breezy Point #303 - Rooftop Deck Panoramic Sunsets · 3 bd · sleeps 9
• Oceanfront Condo w/Balcony, Walk to OC Boardwalk · 3 bd · sleeps 7
• Countryside Modern Stay · 3 bd · sleeps 6
• Huge Downtown House Steps to Beach · 5 bd · sleeps 14
• Ocean City Beach House | Oceanfront Condo · 1 bd · sleeps 5
• Sandpiper Dunes 1009 · 2 bd · sleeps 8
• Golden Sands 1617 · 2 bd · sleeps 8
• Nice Renovated Townhome in the Heart of Ocean City · 2 bd · sleeps 4
• OCHG Oceanfront Villa 3 · 5 bd · sleeps 20
• Pet Friendly Condo Steps to Beach · 3 bd · sleeps 8
• Sea Breeze Cottage | The Inn on Turville Creek · 1 bd · sleeps 4
• Park Place | Waterfront Views + Boat Dock · 5 bd · sleeps 10
• Seize the Bay · 4 bd · sleeps 8
• Family-Friendly Home w/ Hot Tub • Fire Pit• Games · 3 bd · sleeps 7
• Relax on Kent Island in 3 Bedroom Home w/Waterview - Holiday Home · 3 bd · sleeps 11
• Fitzgerald Retreat · sleeps 10
• Carriage on Conduit · 2 bd · sleeps 6
• The Cove House · 3 bd · sleeps 10
• Large Family Getaway - Short Walk To Beach · 3 bd · sleeps 13
• Cool Spring Retreat · 5 bd · sleeps 12
• Lansdowne at 5th ~ 338 · 6 bd · sleeps 12
• Tahitian Sunrise Retreat- Just Steps to the Beach! · 2 bd · sleeps 6
• Sea Watch 318 · 2 bd · sleeps 6
• Five Bedroom Waterfront Home with Lots of Space · 5 bd · sleeps 18
• Little Salisbury Coastal Cottage | Grill + Patio · 2 bd · sleeps 6
• Coastal-Chic · Pool, Bay View & Balcony·Walk2Beach · 2 bd · sleeps 6
• Tamarindo Beach House · 4 bd · sleeps 10
• Luxury Townhome with Pool, Walk to Beach · 4 bd · sleeps 9
• Bayfront Beauty - Shipwreck 102 · 2 bd · sleeps 4
• Parrot Bay Townhouse 30 | Pet Friendly · 3 bd · sleeps 10
• Plaza 106 Direct Ocean Front · 3 bd · sleeps 10
• Harborview Retreat Mansion · 3 bd · sleeps 11
• High Tide @ Lighthouse Bay · 3 bd · sleeps 10
• Coastal Haven at 129th | Ocean View Beach Retreat! · 3 bd · sleeps 6
• Seashell Shores Beach House · 3 bd · sleeps 7
• Royal Views · 3 bd · sleeps 11
• Sea Star 201 · 2 bd · sleeps 6
• Atlantis Oasis - Ocean Front! · 2 bd · sleeps 6
• Four Bedroom West OC Home with Pool and Hot Tub · 4 bd · sleeps 10
• Newly Constructed Condo in the Heart of Ocean City · 3 bd · sleeps 8
• Coconut Grove Cottage | The Inn on Turville Creek · 1 bd · sleeps 4
• Rose's Dream | Screened Porch + Loft · 4 bd · sleeps 10
• Golden Sands Ocean Escape · 2 bd · sleeps 6
• Carousel 2202 | Pools, Ice Rink, Arcade, Gym! · 3 bd · sleeps 12
• El Capitan 503, Oceanfront Boardwalk Best Location · 2 bd · sleeps 8
• Oceanfront Condo with Dual Views · 3 bd · sleeps 10
• Quay 2506 · 3 bd · sleeps 12
• Lookout Landing 6 | Bayfront, Beach Gear & Family Stay · 2 bd · sleeps 7
• Our Place at the Beach | Pool + Bayside Sunsets · 2 bd · sleeps 6
• Midtown Oceanside Condo Just Steps from the Beach · 1 bd · sleeps 5
• Bright & Spacious 3BR Cottage Minutes to DC · 3 bd · sleeps 5
• Sun Village Ocean Front! · 4 bd · sleeps 13
• Sunset Point - 63rd st, 3 BR, Pool · 3 bd · sleeps 8
• Oceanfront Oasis: Pool, Balconies & Beach Access · 6 bd · sleeps 17
• Salty Sands 404 |Steps to Ocean & Dining · 2 bd · sleeps 7
• Downtown Flat • Walk to Dining & Shops • Sleeps 4 · 1 bd · sleeps 4
• Captain’s Crossing · 2 bd · sleeps 6
• 143rd St. Large upscale Townhouse -Sleeps 8 / Pool · 3 bd · sleeps 10
• Hidden Harbour - Bayfront - 2BR, sleeps 6, pool · 2 bd · sleeps 6
• Ocean Pines 3BR House Resort Community · 3 bd · sleeps 6
• Serenity in Ocean Pines | 1 Story Home with Backyard Grill · 3 bd · sleeps 6
• Bella Vista 505 · 3 bd · sleeps 8
• 9400 Building #1106 · 2 bd · sleeps 7
• Ocean / Beachfront 71st/ 4BR/ Pool /Sleeps 11 · 4 bd · sleeps 11
• Two Bedroom Beachfront Condo with Great Amenities · 2 bd · sleeps 6
• Sea Watch- Penthouse, Oceanfront 4 BR, two floors · 4 bd · sleeps 12
• 86th Oceanfront / 4 BRs / sleeps 10 · 4 bd · sleeps 10
• Atlantis 709 · 2 bd · sleeps 6
• Midtown Beach Escape - Ocean Block | Parking | 1E · 3 bd · sleeps 6
• Luxury Deep Creek Lake House w/ Pool & Theater · 8 bd · sleeps 20
• Large Four Bedroom Townhome Close to Boardwalk · 4 bd · sleeps 10
• Alexander 202-B · 3 bd · sleeps 10
• 120th street - Heron Harbour - 2BR sleeps 6, pool · 2 bd · sleeps 6
• Charm City Homestay in Washington Village · 2 bd · sleeps 6
• Tiffanie by the Sea 316A · 2 bd · sleeps 7
• Ocean Vista · 5 bd · sleeps 7
• Luxurious Son Rays 15th street- 3BR, 3BA · 3 bd · sleeps 6
• Mins to Golf & Ocean City! Sleeps 16 w. GameRoom! · 6 bd · sleeps 16
• Condo with Tiki Bar, Walk to Beach · 2 bd · sleeps 6
• Sunset Bay Oasis - Rooftop Pool! · 2 bd · sleeps 7
• Ocean Hideaway 508 · 2 bd · sleeps 8
• Stunning Oceanfront Resort Condo · 2 bd · sleeps 7
• Quay 502 · 2 bd · sleeps 6
• Oceanfront - 72nd street - Oceanview - 2 BR, 2 BA, Sleeps 7 · 2 bd · sleeps 7
• Miss Shell at Lighthouse Bay | Walk to Beach · 3 bd · sleeps 11
• Manor in the Park · 6 bd · sleeps 14
• Seal Beach 2 · 3 bd · sleeps 11
• "Marlin Sunset" - 11th/Bay, 2 BRs, sleeps 6 · 2 bd · sleeps 6
• Waterfront Ocean Pines - 3 Brs with Dock · 4 bd · sleeps 9
• OCHG Beachview 4 · 4 bd · sleeps 15
• Broad Marsh 110E | Large Family Townhome with Pool · 4 bd · sleeps 11
• Luxurious Son Rays 15th street, 4 BR, 4 BA · 4 bd · sleeps 10
• Eastport Easy · sleeps 7
• The Brick House · 5 bd · sleeps 11
• Nicely Updated Three Bedroom Home in Ocean Pines · 3 bd · sleeps 9
• Marigot Beach 307 · 1 bd · sleeps 2
• 4BR house - West OC, Harbor /Assateague- sleeps 9 · 4 bd · sleeps 9
• 6BR Luxury Escape w/ Indoor Pool Boat Dock Avail · 6 bd · sleeps 16
• Century One #1008 · 2 bd · sleeps 6
• Surfside at Robin Drive · 1 bd · sleeps 4
• Direct Oceanfront 4BR/4BA Beach House on 31st Street, Ocean City MD | Sleeps 13, Pet-Friendly, Beach Gear + Bikes Included | Midtown Ocean Views · 4 bd · sleeps 13
• Studio apartment at Sugarloaf Log House · 1 bd · sleeps 2
• Direct Bayfront Condo with Great Location and Pool · 3 bd · sleeps 8
• Sunset Island - 5 BR, Sleeps 12, 2 pools · 5 bd · sleeps 12
• Oceanfront condo with pool, sleeps 4, free Wi-Fi · 1 bd · sleeps 4
• Four Bedroom Oceanside Penthouse with Great Views · 4 bd · sleeps 14
• Five Bedroom Home with Great Amenities in West OC · 5 bd · sleeps 12
• New, Intown Waterfront Townhome wPool & Location! · 3 bd · sleeps 8
• The Taj Guest House · 3 bd · sleeps 6
• Deep in the Heart of Crabtown · 2 bd · sleeps 6
• Serenity Starfish House – Spacious 4-Story Coastal Retreat Near the Beach! · 3 bd · sleeps 11
• Seaside Sanctuary @ Stone Harbor · 4 bd · sleeps 10
• OCHG Beachview 2 · 4 bd · sleeps 15
• OCHG 102 10th St Townhouse A · 3 bd · sleeps 12
• Bird's Eye View · sleeps 5
• South Park · 4 bd · sleeps 6
• The Yellow Door House-Hagerstown · 4 bd · sleeps 10
• Steps to Beach-2nd Floor-Near Convention Center · 3 bd · sleeps 8
• Saltwater Serenity of Long Point · 2 bd · sleeps 4
• Coastal Pines Retreat | Beach Pass & Grill · 3 bd · sleeps 6
• Villa Sole Retreat - Screened Porch & Fire Pit! · 3 bd · sleeps 8
• Canal Front Condo with Pool · 1 bd · sleeps 4
• Blue Horizon at Old Port · 2 bd · sleeps 6
• Bay Breeze Mini Mansion · 3 bd · sleeps 12
• The Salty Deckhouse- Master with Private Balcony! · 4 bd · sleeps 10
• Coastal Modern Retreat | Large Group Getaway on 2 Acres · 6 bd · sleeps 15
• Woodland Retreat | Cozy 3BD in Ocean Pines · 3 bd · sleeps 6
• Lux 8BR Estate Near OCMD-Sleeps23-GameRoom-Firepit · 8 bd · sleeps 22
• 2BR Townhouse on 94th Street · 2 bd · sleeps 6
• Sandy Square 103 · 3 bd · sleeps 8
• Three Bedroom Townhome with Short Walk to Beach · 3 bd · sleeps 10
• Surfcaster 103 · 2 bd · sleeps 6
• Sunset Landing 11 · 2 bd · sleeps 6
• Seatime 407S - Outdoor Pool, Beach! Amazing Aesthetics! · 1 bd · sleeps 4
• Sea Watch 1010 · 3 bd · sleeps 6
• 9400 Building #407 · 2 bd · sleeps 8
• Mariner I 3M · 2 bd · sleeps 9
• Great Value for a Two Bedroom Ocean City Condo · 2 bd · sleeps 4
• Ocean & Bay Panorama | Luxe Corner Escape · 3 bd · sleeps 7
• Bayfront Condo with Stunning Sunset Views · 2 bd · sleeps 8
• Bayview Condo with Pool and Short Walk to Beach · 2 bd · sleeps 6
• Oceanside Condo Just Steps From the Beach in OC · studio · sleeps 4
• Captain Quarters 3BR Townhome · 3 bd · sleeps 11
• Mountaineer Ocean Escape · 2 bd · sleeps 8
• Bahia Vista Unit 201 · 4 bd · sleeps 10
• Century One 1605 · 2 bd · sleeps 6
• Stonegate Cottage · 2 bd · sleeps 6
• Large Four Bedroom Townhome with Nice Amenities · 4 bd · sleeps 12
• Silver Sun 201 · 2 bd · sleeps 5
• High Tide 3BR Townhome North OC · 3 bd · sleeps 9
• Sunchaser Shore Retreat · 2 bd · sleeps 10
• Cori Noel 301 | Expansive Balcony | Outdoor Pool · 3 bd · sleeps 8
• Quiet Bayside Condo, Walk to Beach · 2 bd · sleeps 6
• 110A Newport Bay · 3 bd · sleeps 8
• Windward Waves & Bayview Bliss | Pool + Renovated · 2 bd · sleeps 7
• Serenity by the Sea | Townhome + Kid Friendly Loft · 3 bd · sleeps 11
• Wight Bay North 446 · 2 bd · sleeps 6
• Wight Sands Village 24 · 3 bd · sleeps 10
• Beach Retreat | Pool, Balcony & Coastal Getaway! · 2 bd · sleeps 8
• Sunset Cove 17| Pool + Water Views from Balcony · 2 bd · sleeps 9
• Oceanblock Marlin Retreat | Steps to Beach · 3 bd · sleeps 11
• Porch Life · 3 bd · sleeps 7
• Shore Thing! • Townhome + Gameroom · 3 bd · sleeps 11
• Tiburon Tide Retreat · 2 bd · sleeps 8
• OCHG Beachview 2-2 · 4 bd · sleeps 15
• Oceanfront Condo With Pool - Steps To The Beach · 2 bd · sleeps 6
• Habitat Ct · 6 bd · sleeps 7
• Steps to Beach-1st Floor-Near Convention Center · 3 bd · sleeps 8
• OCHG 102 10th St Townhouse B · 3 bd · sleeps 9
• Fitzgerald House · 2 bd · sleeps 6
• Tern Drive #-14 · 2 bd · sleeps 8
• Lighthouse Seclusion · sleeps 12
• Midtown Beach Escape - Ocean Block | Parking | 1W · 3 bd · sleeps 6
• Direct Oceanfront with Pool - Steps To The Beach · sleeps 4
• Midtown Beach Escape - Ocean Block | Parking | 3W · 3 bd · sleeps 6
• Seashell in the City · 2 bd · sleeps 8
• Midtown Beach Escape - Ocean Block | Parking | 3E · 3 bd · sleeps 6
• Boardwalk One - Studio · studio · sleeps 4
• Ocean City Home w/ Game Room & Free Parking · 5 bd · sleeps 12
• Oceanside Three Bedroom Condo Steps from the Beach · 3 bd · sleeps 6
• Mins to Beach & Golf! Private Pool & Luxe Firepit · 4 bd · sleeps 10
• Oceanside Condo w/Balcony, Steps to Beach · 3 bd · sleeps 6
• Walk-to-Beach Condo with a Pool · 2 bd · sleeps 6
• Sunset Cove Cottage | The Inn on Turville Creek · 1 bd · sleeps 4
• Pet Friendly Water View Cottage · 2 bd · sleeps 4
• Dorchester Drift B: Shore Nest · 3 bd · sleeps 7
• Seaside 66 #200 · 1 bd · sleeps 2
• Beachside Condo: Pool & Private Porch · 2 bd · sleeps 8
• Marigot Beach 507 · 1 bd · sleeps 6
• Oceanfront Condo+Balcony, Steps to Beach · 3 bd · sleeps 8
• Sand Pebbles 304 · 2 bd · sleeps 6
• Retreat at Sunset Landing · 2 bd · sleeps 4
• Seafoam Bliss | Townhome Steps to the Beach · 3 bd · sleeps 10
• Coastal Tides & Pines | Dog Friendly · 3 bd · sleeps 6
• Barefoot Pines Beach Retreat | Fire Pit + Grill · 3 bd · sleeps 6
• Coastal Horizon Haven @ the Makai · 2 bd · sleeps 7
• Phoenix | Oceanfront 2BR - Direct Access to Beach · 2 bd · sleeps 8
• Oceanside 3BR Walk to Boardwalk · 3 bd · sleeps 8
• Sandpiper Dunes 105 · 2 bd · sleeps 8
• The Nautical Nest | 3BD + Nice Walk to the Beach · 3 bd · sleeps 7
• Walk to Beach Condo w/ Pool & Water Views · 3 bd · sleeps 8
• Duck Cove Retreat | Screened Deck + Grill · 3 bd · sleeps 8
• Maresol 304 · 3 bd · sleeps 8
• Bayview Bliss at Bridge Point 225 · 2 bd · sleeps 7
• Seaside Escape Ocean Side Condo · 3 bd · sleeps 8
• Carousel 605 · 2 bd · sleeps 8
• Ocean Block Condo with Pool · 1 bd · sleeps 4
• Braemar Towers 212 · 2 bd · sleeps 6
• Broadmarsh 115C · 4 bd · sleeps 10
• Drift Inn Cottage | The Inn on Turville Creek · 1 bd · sleeps 4
• Plaza 109 · 3 bd · sleeps 8
• Lighthouse Bay Luxury Townhome | Arcade Loft · 3 bd · sleeps 10
• Barbados Sun 306 · 2 bd · sleeps 4
• Three Bedroom Condo with Prime Location and Pool · 3 bd · sleeps 10
• Astoria 107 · 3 bd · sleeps 10
• Sandy Square 101 · 3 bd · sleeps 8
• Blush & Blue at the Irene – Beachfront Balcony + Heated Pool (Open Until October 26th 2026) · 2 bd · sleeps 6
• 765 Deer Point, 3BR townhome, Amazing views from deck with 2 parking spaces · 3 bd · sleeps 8

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