Holiday rentals with a pool in Chincoteague

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chincoteague

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Apartment in Dewey Beach

4.95 out of 5 average rating, 105 reviews

Luxury water-view condo with high-end finishes

Luxury 2-bedroom condo at The Residences at Lighthouse Cove located in the heart of Dewey Beach. This unit features great views of Rehoboth Bay and is only 1 block from the Atlantic Ocean. Easy walk to Dewey Beach’s shops, restaurants, and nightlife. This unit sleeps up to 6. There is a master bedroom with a king bed and in suite bathroom. The second bedroom has a full bunkbed bottom & twin top with trundle that can sleep 5. Lounge at private rooftop pool, fire pits, & grills for Residences

12–19 Dec

£157 per night

Guest favourite

Apartment in Ocean Pines

4.96 out of 5 average rating, 108 reviews

Waterview Retreat

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

18–25 Dec

£123 per night

Superhost

Bungalow in Horntown

4.8 out of 5 average rating, 128 reviews

Nature's retreat @ the Bug-a-Boo. Beaches nearby

We're inside a lovely gated campground community with full amenities @ the club house: Wi-Fi, pool, fishing n crabbing, boat ramp , laundry, and bath houses. The Bug a Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 15 min from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

29 Aug – 5 Sept

£130 per night

Superhost

Apartment in Ocean City

4.85 out of 5 average rating, 100 reviews

2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO

Stunning newly renovated 2 bedroom oceanfront condo in the premiere Golden Sands! Blue Wave is known for its unique 3-tiered wave wall and incredible ocean views from the living room and primary bedroom. SmartTV w/Xbox! Wake up to the sun rising over the ocean right out your bedroom window, and after a cup of coffee on the balcony (included!) head to the building's sun deck,fitness center, lounge, arcades, tennis court, pickleball court,beach volleyball,or indoor/outdoor pools and tiki bar.

25 Oct – 1 Nov

£151 per night

Guest favourite

Cottage in Irvington

4.99 out of 5 average rating, 149 reviews

Peaceful Haven

Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen. **Take advantage of our limited time SPECIAL PRICES**

27 Aug – 3 Sept

£300 per night

Guest favourite

Home in Accomac

4.98 out of 5 average rating, 218 reviews

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

14–21 Oct

£151 per night

Guest favourite

Apartment in Ocean City

4.88 out of 5 average rating, 143 reviews

Ocean Front Sea Terrace 209 Heated Pool

Three bedroom if you include the private den with a Queen Serta pullout Sofa. Low Floor and Rare TWO Parking Passes (2nd spot may not be avaiable May -Sept)! Enjoy your morning coffee on your private ocean front balcony or from the comfort of living room couch. Our ocean front retreat is an end unit (next to stairway- skip elevator lines) with ocean views including large heated pool and tennis court. Conveniently located 88th Street within walking distance of many OC's favorites.

8–15 Jan

£165 per night

Guest favourite

Farm stay in Cardinal

4.94 out of 5 average rating, 109 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Come enjoy all the outdoors has on offer at this secluded, waterfront estate. The spacious studio apartment is fully equipped for comfort. 12 acres of waterfront grounds to enjoy including great outdoor seating, fabulous bayside salt water pool. Fish, canoe and kayak right off the farms private dock. Grill and fire pit. Just 10 mins from the charming villages of Mathews and Gloucesters farm to table amenities. Great local food, music, history and shopping right on the bay!

3–10 Aug

£159 per night

Guest favourite

Tiny home in Cape Charles

4.98 out of 5 average rating, 273 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

5–12 Jan

£237 per night

Guest favourite

Home in Cobbs Creek

4.9 out of 5 average rating, 117 reviews

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

"Now this is the life!" "A little piece of paradise!" "Livin the Dream!" "It doesn't get any better than this!" Just a few thoughts that may cross your mind when you come for a stay at The Cottage at Misti Cove. While the name may be simple, don't let that fool you, for so are the best things in life! Getting a taste of the simple life doesn't mean you have to sacrifice amenities. Here, you'll enjoy resort-like amenities without resort crowds.

4–11 Oct

£208 per night

Guest favourite

Apartment in Rehoboth Beach

4.78 out of 5 average rating, 252 reviews

Right on Silver Lake walk to beach!

On the most beautiful and secluded part of Rehoboth. Have breakfast in your patio right on Silver Lake and then go to the pool or walk to the beach, shopping and restaurants downtown or drive 5 minutes to Tanger Outlets! For your peace of mind we comply with Airbnb COVID-19 cleaning and disinfecting guidelines. In addition we follow CDC guidelines leaving more than 24 hour between guests.

22–29 Dec

£135 per night

Guest favourite

Home in Lusby

5.0 out of 5 average rating, 111 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*Summer is a 1-week minimum, Friday-Friday* Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300 foot private beach. The year-round property has a pier, in-ground pool (May-October) with amazing river views.

25 Jun – 2 Jul

£779 per night