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Search results; Over 1,000 homes in Gwynn

Guest favourite
Home in Gwynn
~ Beautiful Gwynn’s Island Waterfront Home ~
4 bedrooms, 6 beds, 2 private bathrooms
6–11 Jul
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5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
3 bedrooms, 4 beds
22–27 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms, 5 beds
20–25 Sept
4.98 out of 5 average rating, 95 reviews
Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds
11–16 Jul
4.89 out of 5 average rating, 357 reviews
Guest favourite
Cottage in Gwynn
Sunset Haven
3 bedrooms, 4 beds
18–23 Aug
4.89 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
17–22 Aug
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
3 bedrooms, 4 beds
25–30 Jul
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Gwynn
Beachfront Oasis
5 bedrooms, 7 beds
12–17 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds
18–23 Jul
4.91 out of 5 average rating, 11 reviews
Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds
12–17 Jul
Top guest favourite
Home in Cobbs Creek
Millionaire $ Views No Xtra Charge! Hot Tub! POOL!
3 bedrooms, 4 beds
16–21 Aug
4.91 out of 5 average rating, 179 reviews
Top guest favourite
Home in Mathews
Garden Cottage in Downtown Mathews
1 bedroom, 1 king bed
24–29 Aug
4.99 out of 5 average rating, 123 reviews
Top guest favourite
Barn in Cobbs Creek
The Barn at Pond Point - Riverfront Home
3 bedrooms, 5 beds
8–13 Sept
4.95 out of 5 average rating, 136 reviews
Top guest favourite
Home in Mathews County
Oyster Haven on Lanes Creek
2 bedrooms, 2 queen beds
27 Jul – 1 Aug
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Deltaville
Ships Watch On The Bay With Endless Water Views
3 bedrooms, 5 beds
20–25 Jul
5.0 out of 5 average rating, 58 reviews
Guest favourite
Home in Mathews
Quirky cottage in downtown Mathews
2 bedrooms, 3 beds
13–18 Jul
4.9 out of 5 average rating, 103 reviews
Guest favourite
Home in Hudgins
Private Beach Getaway at Finest Chesapeake Bay
3 bedrooms, 7 beds
22–27 Aug
4.96 out of 5 average rating, 28 reviews
Hotel in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 bedroom, 1 king bed
5–10 Jul
New place to stay
Top guest favourite
Cottage in Chesapeake
The Cottage @ Captain Genes - Secluded Waterfront
3 bedrooms, 5 beds
12–17 Sept
4.95 out of 5 average rating, 155 reviews