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Search results; Over 1,000 homes in Gwynn

Cottage in Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
3 bedrooms, 5 beds, 1 bathroom
20–27 Sept
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4.93 out of 5 average rating, 43 reviews
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, 103 reviews
Guest favourite
Cottage in Gwynn
Sunset Haven
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.9 out of 5 average rating, 52 reviews
Top guest favourite
Home in Gwynn
Beachfront Oasis
5 bedrooms, 7 beds, 4 bathrooms
21–26 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Hotel in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 bedroom, 1 king bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds, 1 bathroom
14–19 Sept
4.89 out of 5 average rating, 367 reviews
Top guest favourite
Guest house in Redart
Tiny Island House
1 bedroom, 1 queen bed, WC
29 Sept – 4 Oct
5.0 out of 5 average rating, 15 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 Sept
4.98 out of 5 average rating, 49 reviews
Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
3 bedrooms, 4 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 39 reviews
Guest favourite
Home in Gwynn
~ Beautiful Gwynn’s Island Waterfront Home ~
4 bedrooms, 6 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Gwynn
Mathews Gwynn's Island Chesapeake Bay- Sand Beach!
3 bedrooms, 5 beds, 2 bathrooms
13–18 Oct
4.99 out of 5 average rating, 95 reviews
Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Hudgins
Private Beach Getaway at Finest Chesapeake Bay
3 bedrooms, 7 beds, 2 bathrooms
19–24 Sept
4.91 out of 5 average rating, 35 reviews
Top guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Cobbs Creek
Blue Heron WaterSide
4 bedrooms, 8 beds, 2 bathrooms
12–17 Oct
4.98 out of 5 average rating, 176 reviews
Top guest favourite
Tiny home in Diggs
Stargazer Tiny Cabin
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 234 reviews
Guest favourite
Home in Port Haywood
Relax & Heal Cottage Near Ocean & Forest Retreat
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.94 out of 5 average rating, 68 reviews
Guest favourite
Treehouse in Diggs
Wisteria Treehouse
WC
20–25 Sept
4.93 out of 5 average rating, 80 reviews