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Search results; 497 homes in Grimstead, Gwynn

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Top guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds, 1 private bathroom
20–25 Sept
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4.89 out of 5 average rating, 367 reviews
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Cottage in Gwynn
Sunset Haven
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.9 out of 5 average rating, 52 reviews
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Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms, 5 beds, 2 bathrooms
22–27 Sept
4.98 out of 5 average rating, 103 reviews
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Hotel in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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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
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Top guest favourite
Guest house in Redart
Tiny Island House
1 bedroom, 1 queen bed, WC
4–9 Oct
4.94 out of 5 average rating, 16 reviews
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Home in Gwynn
Beachfront Oasis
5 bedrooms, 7 beds, 4 bathrooms
21–26 Sept
5.0 out of 5 average rating, 16 reviews
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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, 40 reviews
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Cottage in Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
3 bedrooms, 5 beds, 1 bathroom
20–27 Sept
4.93 out of 5 average rating, 43 reviews
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Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 20 reviews
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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
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Home in Gwynn
Island Oasis 4+ acre waterfront house with hot tub
4 bedrooms, 7 beds, 2.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 49 reviews
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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, 14 reviews
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Guest favourite
Home in Hudgins
Private Beach Getaway at Finest Chesapeake Bay
3 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 35 reviews
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Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 4 reviews
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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
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Home in Hudgins
The Boathouse- Chesapeake Bay; Kayakers love it.
4 bedrooms, 7 beds, 3 bathrooms
20–25 Sept
4.82 out of 5 average rating, 110 reviews
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Home in Hallieford
Cozy getaway down by the Bay "GreenBay"
3 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
New place to stay
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Top guest favourite
Cottage in Deltaville
The Little House at Waveland
3 bedrooms, 4 beds, 1.5 bathrooms
29 Sept – 4 Oct
4.84 out of 5 average rating, 201 reviews