
Holiday rentals in Gwynn Island
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Top-rated holiday rentals in Gwynn Island
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Gwynn Island holiday rentals
Other great holiday rentals in Gwynn Island
Superhost

Home in Lancaster
4.63 out of 5 average rating, 19 reviewsPeaceful bay retreat. Hot tub,water views,fire pit
SjaloomRating, 5 stars5 months ago
A spacious home by the water. We celebrated Thanksgiving at this location and it was very special. The views are beautiful, had a fire right by the water and relaxed by the beach. A perfect getaway with family and friends. It has everything you need, the living room is super comfortable and great to relax with the family. The kitchen was spacious making it easy to cook and entertain the family. We loved the hot tub, playing pool and having family dinner. Overall a fabulous experience!! Great host- great communication. Highly recommend
Guest favourite

Apartment in Williamsburg
5 out of 5 average rating, 11 reviewsWyndham Governor's Green (3 BD Deluxe)
GlennRating, 5 stars4 months ago
Great location, private and peaceful. Staff was very helpful and friendly.
Superhost

Home in Cape Charles
5 out of 5 average rating, 3 reviewsSol Mate: Bayfront Bliss – Sunrise to Sunset
AmandaRating, 5 stars8 months ago
Lovely spot, well appointed with everything you need for a beach vacay. Super clean and organized. Comfy beds, awesome backyard, bikes and kayaks to borrow. We had a great stay!
Superhost

Home in North
4.82 out of 5 average rating, 45 reviewsWaterfront Sunsets With Pickleball Court & Hot tub
GregRating, 5 stars3 weeks ago
This is such a unique property! It was perfect for our family. We knew the weather was going to be cold and rainy for ~half our visit, but Jessica’s house did not disappoint. There is so much to do, which resulted in priceless family time. When the weather cleared, we fully enjoyed the outside amenities. The pickleball court, sauna, and hot tub were big hits. Jessica is a great communicator and enabled a memorable Spring Break for our kids.
Guest favourite

Cottage in Gwynn's Island
4.93 out of 5 average rating, 28 reviewsLittle Gray Beach House
BenjaminRating, 5 stars6 days ago
we had an excellent time at the little grey house. its cute and comfy and the view is to die for. please do yourselves a favor and watch the sunrise at least once its beautiful. theres not much on the island itself for food but there are plenty of places to find good food near by. I highly recommend the pizza at southwind pizza. was really good. I promise you will enjoy your stay at. Will hopefully beable to book again next time were down in the area!
Superhost

Home in Williamsburg
4.6 out of 5 average rating, 210 reviewsGR8 Family Vacation Rental
KayteRating, 5 stars2 weeks ago
Even though he was out of town when we arrived, Spence was available by phone and quick to respond. We were charmed by the tangible history of the house, and surprised by how private it is, in spite of its proximity to the street. For us, the vintage upstairs bathroom was an added pleasure, and well worth the signs of age. This is a truly beautiful house for visitors who can appreciate it, and Spence is a great host!
Superhost

Flat in Williamsburg
4.79 out of 5 average rating, 14 reviewsGovernor’s Green 2 Bedroom
LindsayRating, 5 stars6 months ago
Check-in was smooth. Deluxe 2 bedroom was very nice and large enough for my entire party. Beds were comfortable and everything was clean. Sorry we couldn’t stay longer to enjoy the resort amenities - but had a lovely stay. Would stay again.
Top guest favourite

Home in Williamsburg
4.97 out of 5 average rating, 39 reviewsSleeps 12 • 3.9 Miles to Colonial Williamsburg
Matthew Rating, 5 stars3 weeks ago
Really big house decorated with very cool antiques. Plenty of room and everything you need to feel at home. The host is amazing so helpful and is prepared for your situation. Highly recommend this country mansion style house.
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- Virginia Beach Oceanfront
- Resort Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- Kingsmill Resort
- First Landing State Park
- Buckroe Beach and Park
- Golden Horseshoe Golf Club
- Sarah Constant Beach Park
- Water Country USA
- Grandview Beach
- Cape Charles Beachfront
- Grove Beach
- Haven Beach
- Jamestown Settlement
- Royal New Kent Golf Club
- Norfolk Botanical Garden
- Guard Shore
- Ragged Point Beach
- Saint Jerome Beach
- Langford Sand
- Jungle Golf
- Outlook Beach