Situated on Virginia’s Eastern Shore, Chincoteague is a small town on an island with the same name. The island is home to the wild Chincoteague ponies, which have been the subject of mysterious folklore and legend. It also boasts a rich history, pristine beaches, and breathtaking views. Chincoteague Island is also a convenient stopover if you want to visit Assateague Island and the Assateague Island National Seashore, a 37-mile (60-kilometer) stretch of beaches and dunes. Visiting this area offers tourists tranquility and an abundance of wildlife. The town of Chincoteague is home to incredible vacation rentals, some including a lavish private pool to elevate your stay experience. Won’t it be an exhilarating experience to soak up the sun on the beaches during the day and relax by the pool at night? Read on and find the best vacation rentals with private pool in Chincoteague, Virginia.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Stunning architectural gem by the water (from USD 540)
This unique waterfront rental cabin boasts contemporary decor and stunning views. The floor-to-ceiling windows and doors allow natural light and let you enjoy the views from indoors. There is a chef’s kitchen with granite countertops that will be a joy to cook in.
The outdoor spaces offer exceptional entertainment and relaxation opportunities. Relax and enjoy unobstructed views of Oyster Bay on the balcony and the pool area. Cool off in the pool or indulge in a long, warm soak in the six-person hot tub.
Top guest reviews
Amenities & Room:
this house was amazing lots of room to have private relaxation even though the house could fit an armycurtains in a few strategic areas (upstairs bathroom) would be greatit is probably even better when you can use the pool and outside areathe house was beautiful and the hot tub and pool overlooking the water was spectacularCleanliness:
the vacation rental was very cleanHost:
rating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulRead more reviewsLocation:
the location is perfectlocation is great it’s a nice house love the hot tub and pool very spaciousi was very happy with the locationi was very happy with the locationi was very happy with the location
2. Whelks on Willow
Located in the heart of Chincoteague Island, this vacation rental is a cozy, well-appointed home for a large group. It features beautifully decorated bedrooms, a full kitchen, and several outdoor areas for relaxation, including a private pool.
The comfortable furnishings of the rental warmly welcomes you after a day of exploring. In the living room is a fireplace to keep you warm on chilly days. You can prepare a lovely dinner and enjoy it poolside.
If you wish to catch up on work here, there is a dedicated workspace and free Wi-Fi.
Chincoteague, Virginia, United States
28.96 km (18.0 mi) from Eastern Shore Railway MuseumAccommodates: 8
Top guest reviews
Amenities & Room:
this is a lovely place with a ton of roomHost:
super responsive from start to finishRead more reviewsLocation:
ample parking quiet area close to many cute shops restaurants and other activitieswe had a great time and the house was close to town so we could explore
3. Horseshoe Haven
Located approximately 5 miles (8 kilometers) from Assateague Beach, Horseshoe Haven offers a warm and welcoming home for families or a group of friends. This rental offers a private swimming pool and an outdoor shower with hot water. You can sit by the porch and watch the horses graze. You also have convenient access to Maddox Boulevard, the beach, restaurants, and shops.
Adventure lovers can go hiking and biking at the nearby Assateague Island Wildlife Refuge. The host also provides 10 bicycles and 2 kayaks with life jackets for you! The property also has space for parking. Pets are welcome with a fee of 25 USD each.
Chincoteague Island, Virginia, United States
29.29 km (18.2 mi) from Eastern Shore Railway MuseumAccommodates: 8
Top guest reviews
Amenities & Room:
the air conditioning was very nice to come back to after a day at the beachwas a wonderful vacation there was plenty of room for our family of 7we loved our stay we enjoyed the outdoor patio the pool the badminton field and the hoststhe pool is pretty nice too and of course the large backyard/front yardbest screened in porch i've ever seen it has hammock chairs ping pong and comfortable seating for 10Cleanliness:
clean with everything you needthe house was clean and cozythis is a special place and was clean and comfortablethe beds were all very comfortable and place was cleanthe beds were very comfy and everything was very cleanHost:
he was a wonderful hostvery nice hospitality & host nearby to respond to all questionsthe hosts were happy to help if we needed anything or had any questionsthe hosts are great and always availablevery very friendly hostsRead more reviewsLocation:
it’s super close to everythingthe location is in a quiet neighborhood but easily accessiblegreat place in a great locationthis house is in a great location only a few blocks from townthe house is in a perfect location for families with small children
4. Cedar Gables (from USD 383)
Cedar Gables gives guests a waterfront location with impeccable amenities and facilities. This lovely property has five bedrooms, each equipped with a fireplace and a private bath with a tub. It may be the perfect accommodation if you’re planning to travel with your family.
Outdoors, you will find a private pool and a hot tub with a tiki bar. You can enjoy fishing on the boat dock. Sitting on the screened patio watching the sunset is something to look forward to.
The rental ensures that you have all the essentials for an unparalleled stay, including a hairdryer, laundry facilities, TVs, air conditioning, and a dedicated workspace.
Top guest reviews
Read more reviewsLocation:
a great house in a wonderful location that’s ideal for large groups and families
Superhost
5. Beautiful creekfront home with a private dock (from USD 325)
Are you looking for a luxurious vacation rental for your family? Consider this spacious rental that sits peacefully on 2.3 acres (0.9 hectares) of creekside land. All the rooms have a mesmerizing view of Nassawadox Creek, where you can enjoy fishing, crabbing, or kayaking. The host has two kayaks for your group.
Once you return from an exciting day outdoors, take a dip in the private pool on the deck and watch the sunset. After, you can prepare a feast in the fully equipped kitchen. If you need any groceries, you’ll find a grocery store in Exmore, Virginia, located only 15 minutes away.
Top guest reviews
Amenities & Room:
the deck seating is a comfortable place to spend watching the water and the birdsCleanliness:
the house was clean and well appointed with everything you need for a relaxing stayHost:
you have privacy while also having your property managers/hosts just moments away for supportnancy and ben are very sweet hosts - perfect balance of providing privacy while supporting needsRead more reviewsLocation:
the house the location and friends made an awesome weekend
6. Clifton House (from USD 325)
Expanding over 4,000 square feet (371.6 square meters) is the historic Clifton House. This stately waterfront estate is a fine choice for history buffs. The property dates back to 1835 and was built by Colonel John Wise, naming it after his home in England. You’ll be able to visit the Wise family graveyard nearby.
The property is spread across two floors, with high ceilings, wood floors, and large rooms equipped with great facilities. The first floor is the main living and entertainment area, including a family room, a kitchen with a fireplace, a game room, and a library.
The property’s top features are a swimming pool, a freshwater pond, and a dock. There is an expansive waterfront lawn to enjoy your nightly strolls.
Top guest reviews
Amenities & Room:
the air conditioning kept the house at a cool temperature and lowered the humidity nicelycomfortable for our 8 person family that includes 6 kiddos of all agesalso it is a perfect set up for kids with separate fences for the pool and yardCleanliness:
the house was huge clean and well appointed for gueststhe home was clean and very comfortableHost:
pete the property manager was very responsivethe pool man and yard man provided friendly and efficient servicehe was very responsive on everything and made check-in really easythe locals were super helpful with suggestions for finding anything we neededRead more reviewsLocation:
it is a great value and a great place to create positive family memoriespool was perfect location was perfect and the house met all of our needspeace of mind for myself but they thought it was an awesome sleep over beautiful place to stay
7. Leatherbury Point Guest House (from USD 243)
Leatherbury Point Guest House, designed by the late architect Lewis Rightmier, is conveniently located five minutes from Onancock, Virginia. What makes this property great is the waterfront view from every room. You can relax outdoors on the dock or in the pool. There is an outdoor play area for children, too. Moreover, two kayaks are available for kayaking, fishing, and crabbing.
If you wish to stroll around the area, a five-minute drive takes you to Onancock, where you will find restaurants, boutiques, and art shops, among others.
Top guest reviews
Cleanliness:
the house was clean and comfortablethe property is beautiful and the pool is clean as perfectRead more reviewsLocation:
despite some cool/wet weather we thoroughly enjoyed the town and locationtown nearby was great for walking around and lunch/dinner
Enjoy a unique island getaway in Chincoteague
You can fully embrace the beauty of Chincoteague and indulge in multiple activities on the water in this stunning town. Book a stay in any of the dreamy vacation rentals above and enjoy a unique island getaway in Chincoteague.
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