
Vacation 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.
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Popular amenities for Chincoteague rentals with a pool
House rentals with a pool

New property with private pool! Sleeps 10
Exactly as described, great space! Bedrooms, bathrooms and kitchen brand new and super high end appliances. Living room space comfortable and well appointed. Highly recommend!

Poolside Paradise - Location!
This spacious 3 bed, 2 bath home is perfect for families seeking comfort and convenience. The generous living space offers plenty of room for everyone, with well-sized bedrooms and bathrooms. The dining area was great for meals, and the kitchen is equipped with appliances and ample counter space. One of the standout features is the home's prime location, directly across from the community pool, making it ideal for summertime fun and relaxation. The neighborhood is friendly and safe, with excellent restaurants nearby. This home truly offers the best of both comfort and convenience, making it a perfect choice for families looking to vacation in OC.

Dodd House Beach Home w/private pool and hot tub
Lynn and Brian’s house was amazing. It was perfect for our large group! The house had everything we needed and more. The hot tub and outdoor area were a huge plus! The house was very clean and they supplied us with sheets and towels which was a huge help. Brian was very responsive and super easy to communicate with. Couldn’t have asked for a better house or hosts!

Spacious Living in Rehoboth, with a Pool
Lovely place to stay! My family and I had our Christmas here and it was the perfect space. It was comfortable, came well stocked, and had nice touches throughout the home.

Blue Heron WaterSide
So glad we found this gem of a location and grateful to our hosts for sharing it with us! Was the perfect quiet weekend getaway for the two families that stayed, and plenty for our tweens and teens to do. We enjoyed fishing and crabbing from the dock and appreciate the generosity of the hosts allowing us to use the SUP, kayak, etc. Laura was very helpful in all communications, before and during our stay. Would definitely stay again!

Secluded beach beauty with private, heated pool
This is a great property! The house is gorgeous, the grounds are clean, kept and very private. The house was fully stocked with kitchenware, pool accessories, & decorated tastefully. A lot of delicate artwork and intentional decor- (if traveling with a young child, one needs to watch them closely :) Re: the beds- my 7 year old described it as “sleeping on clouds!” - very comfy! The area is close (2-3 min) to outlet shops and a bunch of restaurants on Costal Highway 1 and about a 6 min drive to the Rehoboth pier. It’s also a central location to other neighboring beach towns.

Slps 6 | Comm. Pool | PetsOK | WD | Bikes | Kayaks
Such a perfect mix of private and secluded but easy access to the beach. Loved the fire pit. Family had a great time, house had everything needed for the weekend.

Bluewater Beach House - "Under New Management!"
The house was in a great location - walkable to beach and town but on a quiet street. It was close to the main road with stores and conveniences. It had two sun porches which were not shown in the photos and were great for outdoor relaxation.
Condo rentals with a pool

Lovely 2BR Condo - Rehoboth/ Dewey
Michelle's place was spacious and well-appointed for myself and four other people. The water pressure was great, there was plenty of hot water for showers, and it was conveniently located. The neighborhood was quiet, and while we didn't have time to enjoy the amenities, the screened-in porch was lovely to enjoy and, best of all, free! The beds were firm and comfortable; the apartment was very clean! Thanks for a great stay, Michele!

Ocean View, Large Condo, Heated Pool
I had a fantastic stay! The place was immaculately clean—you can tell the host really takes pride in maintaining a spotless and welcoming space. Everything felt fresh, tidy, and well-cared for, which made it so easy to relax and feel at home. Beautiful view!! Communication was smooth, and check-in was simple. Highly recommend to anyone looking for a comfortable and exceptionally clean stay!

Waterfront Condo With Olympic size swimming pool
James was an amazing host. He was responsive, helpful, and kind. The condo was beautiful, clean, and perfect for our family. The neighbors were also very kind and welcoming. My children loved the pool and walking the bay. The views were second to none and the location was perfect since it was minutes away from restaurants, stores, and Bethany beach. We will definitely be booking again!

Condo with Pool in the Heart of OC
Stayed at this condo for Oceans Calling—which was about 3 miles away. It was tidy and welcoming and fit our needs well.

Ocean View Condo W/ Indoor and Outdoor Pool
Our family stayed here for a brief weekend trip. The place was cozy, with everything you need inside and out, and the view! I felt spoiled sitting on the patio watching the ocean while I drank my coffee in the mornings. The condo itself was lovely, and the location was great, with easy access to stores and city transportation. I was a little disappointed that the property pool and kiddy area wasn’t open yet, but we had an entire ocean at our finger tips. Everything from start to finish was easy to navigate. We will definitely be back in the future!

Bayfront Condo 46th St *2 POOLS*Free Linens/Towels
I can’t say enough how beautiful this condo is! It was absolutely spotless and the views are worth every penny! Felt right at home!

Stunning 2 bedroom with pool
My husband and I love staying in Airbnb‘s. I am pretty anal about cleanliness. I am a teacher and also a cleaning lady myself, and thought this was the cleanest place I’ve ever stayed at. The decor was so crisp and clean. I felt comfortable sitting on the couch, the beds, etc. They were very accommodating when we needed to talk to them. I totally recommend this place!

Paradise At Sunset Island In OC
We love staying at Sunset Island. This is the first time in a condo and it was perfect!
Quick stats about vacation rentals with a pool in Chincoteague
Total rentals
140 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
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- Chesapeake Bay
- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Jolly Roger Amusement Park
- Northside Park
- Jolly Roger at the Pier
- Bayside Resort Golf Club
- Snead Beach
- Delaware Seashore State Park
- Peninsula Golf & Country Club
- Assateague Beach
- Wallops Beach
- Bear Trap Dunes
- Trimper Rides of Ocean City
- Plantation Lakes Golf and Country Club
- Coin Beach
- Assateague State Park
- Parramore Beach
- Guard Shore
- Lost Treasure Golf
- The Links at Lighthouse Sound
- Fenwick Island State Park Beach
- Gargathy Beach
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