House in Chincoteague Island, VA
9 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Check out Chincoteague's newest Piney Island vacation rental! Hailey's Round House is in a prime location on Chincoteague, in a quiet development road but just a short walk to the bridge to Assateague and the Maddox Boulevard shops and restaurants! You could take a bicycle or short drive to the Assateague beach and access to all of the bicycle trails around Chincoteague and Assateague to enjoy the wild ponies or many of the restaurants on Chincoteague.
Hailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed. You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay!
- Linens and towels are included with your reservation.
- No smoking is permitted on the premises.
- No pets are permitted on the premises.
- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
Hailey's Round House is a recently renovated, beautiful 3 bedroom home with 2 bathrooms. The luxury porcelain floors throughout will leave you feeling entranced from the moment you walk through the door. Spacious, thoughtful, aesthetically pleasing, and comfortable are just a few words to describe what you will experience at Hailey's Round House. This home offers first floor living, a huge screened porch, quartz countertops, ample deck space, seclusion as well convenience. On the first floor, you will find a full bath with walk in tiled shower, as well as a complete living room, and bedroom featuring a full sized bed. You can reach the second floor by a private exterior entrance, or from the winding spiral staircase located inside. Upstairs you will find a second living room as well as two more bedrooms and another full bathroom with a tub. One bedroom features a full sized bed and the third is perfect for the kids, offering a twin as well as a full. While there are many focal points of this fabulous home, we are certain most of your time will be spent on the expansive deck, enjoying the sounds of nature and the deer who frequently visit the yard or downstairs in the screened porch. Hailey's Round House is located in one of the Island's most desired locations of Piney Island! It is close to the beach and ready to host your vacation stay!
- Linens and towels are included with your reservation.
- No smoking is permitted on the premises.
- No pets are permitted on the premises.
- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.
Amenities at Hailey's Roundhouse - Unique Piney Island Home w/ Water Access!
Non-smoking
No pets allowed
Family friendly
Map of Chincoteague Island, VA
Ratings and reviews
10 / 10Outstanding·Jul 2026
We liked: spacious interior living spaces, large kitchen area with dishwasher - microwave - adequate appliances (we like to eat most meals 'at home'), separated upstairs and downstairs living and sleeping areas, nice washer and dryer upper level, good a/c coverage throughout whole home, outside stairs to upper level and deck, lower screened porch with outdoor furniture, accessible location between beach and commercial areas, somewhat private and quiet location even though other homes are nearby.Disappointments: refrigerator ice-maker didn't work, screened porch is in poor shape with torn screens, dirty floors, screen doors need replacing, kitchen could use a few more items for food storage (pitchers, eating utensils), another table would be helpful, no curtain or privacy cover for downstairs bathroom window, large windows had hand and finger smudges on them, outdoor grill was very dirty (we would have to clean it to use it), no simple mop for keeping floors clean. Very distracting was the boat parked out front with standing water full of mosquito larvae adding to the amount of biting insects, unmarked tripping hazard next to the driveway with a rebar handle at ground level for concrete sewer top, no outdoor shower (just a hose).In spite of these disappointments, we'd likely return to this convenient location with the spacious interior living areas that have been updated with the clean and finished appearance.
10 / 10Outstanding·Aug 2025
Had a great time at Hailey’s roundhouse
10 / 10Outstanding·Sep 2024
The house was very cute. It was extremely quiet at night which was nice. Very close to beach and restaurants.
6 / 10Average·Aug 2024
While the location of the property is great, and the neighborhood is quiet, we thought there should have been some improvements done and more supplies provided. Specifically, the spiral staircase is wobbly, the screened porch door does not stay closed as the latch is not properly installed/old, every light including nightstands in the house is very bright white, and there is an unpleasant odor in the house. In terms of supplies, the listing said "no linens" but it did not say "no towels" when we booked it, so we had no bath or kitchen towels which is usually not the case when we stay at other VRBO properties. They added "no towels" to the listing after I asked them about the towels. We are not staying there again although we did make the most out of it. We just hope this review helps bring changes to the house and the management.
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Top rated by guests
9.2Outstanding
(6 Ratings)
"We liked: spacious interior living spaces, large kitchen area with dishwasher - microwave - adequate appliances (we like to eat most meals 'at home'), separated upstairs and downstairs living and slee..."
Doug S.Don't miss out! Price and availability may change
