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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
20–25 Sept
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4.99 out of 5 average rating, 93 reviews
Top guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms, 5 beds, 2 bathrooms
26–31 Aug
4.98 out of 5 average rating, 100 reviews
Room in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 king bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Guest house in Redart
Tiny Island House
1 bedroom, 1 queen bed, WC
15–20 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 35 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, 14 reviews
Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Hudgins
Private Beach Getaway at Finest Chesapeake Bay
3 bedrooms, 7 beds, 2 bathrooms
24–29 Aug
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Gwynn
Island Oasis 4+ acre waterfront house with hot tub
4 bedrooms, 7 beds, 2.5 bathrooms
15–20 Aug
4.98 out of 5 average rating, 48 reviews
Guest favourite
Cottage in Gwynn
Sunset Haven
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Home in Port Haywood
Relax & Heal Cottage Near Ocean & Forest Retreat
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 61 reviews
Guest favourite
Home in Gwynn
~ Beautiful Gwynn’s Island Waterfront Home ~
4 bedrooms, 6 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds, 1 bathroom
22–27 Aug
4.89 out of 5 average rating, 361 reviews
Top guest favourite
Home in Mathews County
Oyster Haven on Lanes Creek
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 19 reviews
Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Room in Cardinal
Wtrfrnt aptmnt w/pool/dock on private farm
2 beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 226 reviews
Guest favourite
Cottage in Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
3 bedrooms, 5 beds, 1 bathroom
23–30 Aug
4.93 out of 5 average rating, 41 reviews
Top guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Tiny home in Diggs
Stargazer Tiny Cabin
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 231 reviews