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Featured Cottages in Gwynn

Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (302)
"We had a very enjoyable stay. Peaceful, quiet, tranquil. Thoroughly enjoyed it. Met with longtime friends for a getaway. The place isn't fancy, but we weren't looking for fancy, just a quiet hideout. Would stay again."
Cottage on a Private Island in the York River
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (241)
"Excellent base for exploring Williamsburg, Yorktown and Jamestown. Beautiful historic cottage on expansive grounds. Dead quiet."
Historic Cottage on Ware River Estate
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (60)
"This was the most amazing weekend we have had at a VRBO property! The location is absolutely unbeatable and the cottage is brimming with character and ambiance. We loved every minute of our stay and will definitely return. This property is a gem and we feel so blessed to have found this listing."
Oceanfront White Stone Cottage w/ Private Beach!
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Riverfront Cottage: Fire Pit & Kayaks
9.8 out of 10, Exceptional, (25)
"It was beautiful. We loved wake up to the beautiful water everyday."
Riverfront Cottage: Fire Pit & Kayaks
The Little Blue Cottage - Topping : Waterfront!
9.8 out of 10, Exceptional, (28)
"Inside decor was spot on. Kitchen was well-stocked, and we enjoyed the dock and fishing. Host was a great communicator."
The Little Blue Cottage - Topping : Waterfront!
Peaceful Waterfront Cottage on VA’s Northern Neck
10.0 out of 10, Exceptional, (87)
"We loved our stay at Fred’s property. Unfortunately the weather didn’t cooperate enough for us to enjoy the water, but the views and cozy cottage provided a relaxing time away nonetheless. Location was great — off the beaten path but still a quick drive to town."
Peaceful Waterfront Cottage on VA’s Northern Neck
Have you made your summer vacay plans yet at the Rivah in Irvington?
10.0 out of 10, Exceptional, (264)
"Classic Northern Neck cottage beautifully maintained and wonderfully comfortable."
Have you made your summer vacay plans yet at the Rivah in Irvington?
Bubba Butler's Cottage
Bubba Butler's Cottage
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
10.0 out of 10, Exceptional, (177)
"Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back."
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
Sunflower Cottage - Waterfront; Outdoor shower!
10.0 out of 10, Exceptional, (2)
"Pleasant, relaxing, well-kept. Very convenient being right on the bay. Excellent customer service. Would definitely stay here again!"
Sunflower Cottage - Waterfront; Outdoor shower!
Waterfront Cottage with pool
10.0 out of 10, Exceptional, (41)
"Location, location, location! We were so surprised to find this extraordinary property available at the last minute! Everything about the cottage was charming and we both enjoyed ourselves immensely. The tranquil setting, tiny beach and wildlife just added to the experience. My husband took lots of lovely pictures while I enjoyed a book under the trees. We had amazing meals in the village of Gloucester Courthouse and antiquing in nearby Mathews. The Owner was prompt in answering questions and...
Waterfront Cottage with pool
Romantic Waterfront Abode with Patio & Dock!
9.8 out of 10, Exceptional, (40)
"We absolutely loved our stay on Sturgeon Creek. The cottage was perfect and had everything we needed. Incredible view of the water and the sunsets were amazing. We will definitely be back! Thanks so much making our getaway so special! Pam & Tony"
Romantic Waterfront Abode with Patio & Dock!
The Crab Shack on Carter's Creek
10.0 out of 10, Exceptional, (64)
"Staying at the Crab Shack was wonderful. It is so beautiful, simple and peaceful. Carlisle has thought of everything and was so helpful. We loved our daily excursions but loved coming "home" to the Shack. A reminder to pause and slow down! Simple but Significant...."
The Crab Shack on Carter's Creek
Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf
10.0 out of 10, Exceptional, (72)
"We absolutely LOVE the Fish House at Grandview on the Bay. This was the third time we have been here and Karla and Dave never disappoint, they are so friendly and their property is stunning from the home, putt putt, pool and the VIEWS are ⭐️⭐️⭐️⭐️⭐️"
Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf
Restored 1920's Cottage on 1 Acre w/ Fire Pit
9.4 out of 10, Exceptional, (44)
"Our grandchildren came for several visits and overnights. It was great. The cottage is very user friendly and was quiet. The surrounding areas uncluding paddock was a bonus for our Shetland sheepdogs. The walking trails were fine. We had a fantastic stay."
Restored 1920's Cottage on 1 Acre w/ Fire Pit
Urbanna Waterfront Retreat: Pier & Gas Grill!
9.6 out of 10, Exceptional, (8)
"Had a great time staying at this rental. Great view and amenities. Fully stocked kitchen and supplies. If you just want to relax and take in the view or maybe do some fishing this is a great place to visit."
Urbanna Waterfront Retreat: Pier & Gas Grill!
Relaxing Riverfront Cottage w/ Boat Dock!
9.8 out of 10, Exceptional, (22)
"This was seriously one of the best rentals we've ever stayed! It was very clean, all the "extras" were of great quality and very well thought-out....extra blankets, fully stocked kitchen with every appliance you could need, ample towels and bath supplies, complete outdoor rec gear; just to name a few. The neighborhood was quiet and the view was amazing! I can't say enough about the quality and attention to detail this house had. Thanks for everything!"
Relaxing Riverfront Cottage w/ Boat Dock!
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg
10.0 out of 10, Exceptional, (116)
"Beautiful and very clean cottage!Nice place to relax and enjoy your vacation."
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg
Waterfront with Private Pier and Tranquil Water views!
10.0 out of 10, Exceptional, (89)
"The home is charming and equipped with almost everything a guest could need. The location is great. Views are spectacular. We caught fish, took long walks, and explored the area. Shops and restaurants in the middle peninsula and northern neck area that we visited were very nice. The hosts were very responsive. Will try to visit every year."
Waterfront with Private Pier and Tranquil Water views!
3 BR Bay Home w Private Dock & all the Amenities
10.0 out of 10, Exceptional, (8)
"We wanted a place to get away with our kids before the hustle and bustle of the school year and sports start. It was a perfect home with lots of great amenities and a great location!"
3 BR Bay Home w Private Dock & all the Amenities
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See all available properties in Gwynn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Gwynn

Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
10.0 out of 10, Exceptional, (177)
"Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back."
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
10.0 out of 10, Exceptional, (210)
"We love this place... it's our third time there and it's always clean and feels like home. Big plus.... we get to take our dog. ❤️"
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
6.0 out of 10, (1)
"The property was nice but i would call it pet tolerant, not friendly. I booked this for my children and there two dogs instead of hotel. If i had known all the rules before i booked i wouldn't have. Out of two nights, they only stayed one because they couldn't relax with their animals."
The price is NZ$676
includes taxes & fees
29 May - 30 May
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.