7 Best Vacation Rentals With Private Pool In Chincoteague, Virginia - Updated 2024

Anam
Anam 
Contributing Writer
Updated
| 4 min read

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 May 29, 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.

Stayed at this property?

32.25 km (20.1 mi) from Eastern Shore Railway Museum
27 reviews  
House 16 Guests 3 Bedrooms 4 Bathrooms

Accommodates: 16
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
this house was amazing lots of room to have private relaxation even though the house could fit an army
curtains in a few strategic areas (upstairs bathroom) would be great
it is probably even better when you can use the pool and outside area
the house was beautiful and the hot tub and pool overlooking the water was spectacular
Cleanliness:
the vacation rental was very clean
Host:
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
the location is perfect
location is great it’s a nice house love the hot tub and pool very spacious
i was very happy with the location
i was very happy with the location
i was very happy with the location
Read more reviews

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.

Stayed at this property?
Chincoteague, Virginia, United States
28.96 km (18.0 mi) from Eastern Shore Railway Museum
13 reviews   Wifi Available
ENTIRE HOME 6 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
this is a lovely place with a ton of room
Host:
super responsive from start to finish
Location:
ample parking quiet area close to many cute shops restaurants and other activities
we had a great time and the house was close to town so we could explore
Read more reviews

3. Horseshoe Haven (from USD 191)

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.

Stayed at this property?
Chincoteague Island, Virginia, United States
29.29 km (18.2 mi) from Eastern Shore Railway Museum
54 reviews   Wifi Available
Entire guesthouse 5 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the air conditioning was very nice to come back to after a day at the beach
was a wonderful vacation there was plenty of room for our family of 7
we loved our stay we enjoyed the outdoor patio the pool the badminton field and the hosts
the pool is pretty nice too and of course the large backyard/front yard
best screened in porch i've ever seen it has hammock chairs ping pong and comfortable seating for 10
Cleanliness:
clean with everything you need
the house was clean and cozy
this is a special place and was clean and comfortable
the beds were all very comfortable and place was clean
the beds were very comfy and everything was very clean
Host:
he was a wonderful host
very nice hospitality & host nearby to respond to all questions
the hosts were happy to help if we needed anything or had any questions
the hosts are great and always available
very very friendly hosts
Location:
it’s super close to everything
the location is in a quiet neighborhood but easily accessible
great place in a great location
this house is in a great location only a few blocks from town
the house is in a perfect location for families with small children
Read more reviews

4. Cedar Gables (from USD 1100)

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.

Stayed at this property?
Chincoteague Island, Virginia, United States
31.75 km (19.8 mi) from Eastern Shore Railway Museum
12 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 12 Guests 5 Bedrooms 6 Bathrooms

Accommodates: 12

Top guest reviews
Location:
a great house in a wonderful location that’s ideal for large groups and families
Read more reviews

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.

Stayed at this property?

41.84 km (26.0 mi) from Eastern Shore Railway Museum
10 reviews   Wifi Available
House 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the deck seating is a comfortable place to spend watching the water and the birds
Cleanliness:
the house was clean and well appointed with everything you need for a relaxing stay
Host:
you have privacy while also having your property managers/hosts just moments away for support
nancy and ben are very sweet hosts - perfect balance of providing privacy while supporting needs
Location:
the house the location and friends made an awesome weekend
Read more reviews

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.

Stayed at this property?

11.0 km (6.9 mi) from Eastern Shore Railway Museum
22 reviews   Wifi Available
estate 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
the air conditioning kept the house at a cool temperature and lowered the humidity nicely
comfortable for our 8 person family that includes 6 kiddos of all ages
also it is a perfect set up for kids with separate fences for the pool and yard
Cleanliness:
the house was huge clean and well appointed for guests
the home was clean and very comfortable
Host:
pete the property manager was very responsive
the pool man and yard man provided friendly and efficient service
he was very responsive on everything and made check-in really easy
the locals were super helpful with suggestions for finding anything we needed
Location:
it is a great value and a great place to create positive family memories
pool was perfect location was perfect and the house met all of our needs
peace of mind for myself but they thought it was an awesome sleep over beautiful place to stay
Read more reviews

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.

Stayed at this property?

13.17 km (8.2 mi) from Eastern Shore Railway Museum
6 reviews   Wifi Available
House 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Cleanliness:
the house was clean and comfortable
the property is beautiful and the pool is clean as perfect
Location:
despite some cool/wet weather we thoroughly enjoyed the town and location
town nearby was great for walking around and lunch/dinner
Read more reviews

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.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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I am an aspiring content writer with a knack for details and a keen sense of observation. With a zeal for exploring new destinations and diving into their history and culture, I seek opportunities...Read more

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