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Search results; Over 1,000 homes in Gwynn

Top guest favourite
Home in Gwynn
Mathews Gwynn's Island Chesapeake Bay- Sand Beach!
3 bedrooms, 5 beds, 2 private bathrooms
17–22 Aug
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4.99 out of 5 average rating, 90 reviews
Hotel in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 bedroom, 1 king bed, 1 bathroom
14–19 Jul
New place to stay
Top guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 96 reviews
Guest house in Redart
Tiny Island House
1 bedroom, 1 queen bed, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.89 out of 5 average rating, 357 reviews
Guest favourite
Cottage in Gwynn
Sunset Haven
3 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
4.89 out of 5 average rating, 47 reviews
Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 30 reviews
Guest favourite
Cottage in Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
3 bedrooms, 5 beds, 1 bathroom
16–23 Aug
4.93 out of 5 average rating, 41 reviews
Guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Home in Mathews
Garden Cottage in Downtown Mathews
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 126 reviews
Top guest favourite
Home in Gwynn
Beachfront Oasis
5 bedrooms, 7 beds, 4 bathrooms
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Mathews County
Oyster Haven on Lanes Creek
2 bedrooms, 2 queen beds, 1 bathroom
27 Jul – 1 Aug
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in White Stone
1891 Coastal Charmer: fully renovated farmhouse
3 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
4.99 out of 5 average rating, 140 reviews
Top guest favourite
Flat in Cobbs Creek
Peaceful Private Waterside Apartment
2 bedrooms, 2 queen beds, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Port Haywood
Relax & Heal Cottage Near Ocean & Forest Retreat
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 56 reviews
Guest favourite
Cottage in Diggs
Chesapeake Bay Beach Front cabin
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.9 out of 5 average rating, 31 reviews
Guest favourite
Home in Mathews
Quirky cottage in downtown Mathews
2 bedrooms, 3 beds, 1 bathroom
18–23 Aug
4.91 out of 5 average rating, 106 reviews
Top guest favourite
Cabin in Deltaville
"The Little Red Cabin" aka The Galley
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 344 reviews