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Search results; Over 1,000 homes in Gwynn
Over 1,000 homes in Gwynn
Guest favourite
Guest favourite
Home in Gwynn
~ Beautiful Gwynn’s Island Waterfront Home ~
4 bedrooms
,
·
6 beds
,
·
2 private bathrooms
6–11 Jul
6–11 Jul
$2,713 SGD
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for 5 nights
$2,713 SGD for 5 nights
,
·
5.0 out of 5 average rating, 42 reviews
5.0 (42)
Top guest favourite
Guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,903 SGD
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for 5 nights
$2,903 SGD for 5 nights
4.98 out of 5 average rating, 95 reviews
4.98 (95)
Top guest favourite
Guest favourite
Home in Gwynn
Beachfront Oasis
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
4 bathrooms
4 bathrooms
12–17 Aug
12–17 Aug
$6,667 SGD
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for 5 nights
$6,667 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top guest favourite
Guest favourite
Home in Hudgins
Oyster Haven- private beach front home 3 bedrooms
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Jul
25–30 Jul
$2,237 SGD
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for 5 nights
$2,237 SGD for 5 nights
5.0 out of 5 average rating, 29 reviews
5.0 (29)
Guest favourite
Guest favourite
Cottage in Gwynn
Sunset Haven
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
18–23 Aug
18–23 Aug
$1,494 SGD
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for 5 nights
$1,494 SGD for 5 nights
4.89 out of 5 average rating, 47 reviews
4.89 (47)
Top guest favourite
Guest favourite
Home in Gwynn
Mathews Gwynn's Island Chesapeake Bay- Sand Beach!
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
17–22 Aug
17–22 Aug
$2,667 SGD
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for 5 nights
$2,667 SGD for 5 nights
4.99 out of 5 average rating, 89 reviews
4.99 (89)
Top guest favourite
Guest favourite
Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
11–16 Jul
11–16 Jul
$2,480 SGD
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for 5 nights
$2,480 SGD for 5 nights
4.89 out of 5 average rating, 357 reviews
4.89 (357)
Home in Hudgins
Gwynn's Island Gem | Private Beach & Bay Views
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
12–17 Jul
12–17 Jul
$3,294 SGD
$2,812 SGD
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for 5 nights
Guest favourite
Guest favourite
Home in Gwynn
The Sandbar on Gwynn’s Island
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
22–27 Aug
22–27 Aug
$3,243 SGD
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for 5 nights
$3,243 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favourite
Guest favourite
Cottage in Gwynn
320 Water View and Access Retreat - Fiddlers Green
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
18–23 Jul
18–23 Jul
$1,948 SGD
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for 5 nights
$1,948 SGD for 5 nights
4.91 out of 5 average rating, 11 reviews
4.91 (11)
Hotel in Gwynn
Cricket Hill House — Waterfront Suite, 2 East
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,486 SGD
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for 5 nights
$1,486 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Home in Gwynn
Island Oasis 4+ acre waterfront house with hot tub
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2.5 bathrooms
2.5 bathrooms
15–20 Aug
15–20 Aug
$3,275 SGD
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for 5 nights
$3,275 SGD for 5 nights
4.98 out of 5 average rating, 46 reviews
4.98 (46)
Guest favourite
Guest favourite
Home in Hudgins
Private Beach Getaway at Finest Chesapeake Bay
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
22–27 Aug
22–27 Aug
$2,621 SGD
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for 5 nights
$2,621 SGD for 5 nights
4.96 out of 5 average rating, 28 reviews
4.96 (28)
Top guest favourite
Guest favourite
Home in Mathews County
Oyster Haven on Lanes Creek
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
27 Jul – 1 Aug
27 Jul – 1 Aug
$1,893 SGD
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for 5 nights
$1,893 SGD for 5 nights
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Guest favourite
Guest favourite
Home in Hudgins
The Boathouse- Chesapeake Bay; Kayakers love it.
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
16–21 Sept
16–21 Sept
$3,170 SGD
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for 5 nights
$3,170 SGD for 5 nights
4.83 out of 5 average rating, 109 reviews
4.83 (109)
Top guest favourite
Guest favourite
Home in Cobbs Creek
Blue Heron WaterSide
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
2 bathrooms
2 bathrooms
8–13 Sept
8–13 Sept
$3,261 SGD
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for 5 nights
$3,261 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 171 reviews
4.98 (171)
Guest favourite
Guest favourite
Home in Hallieford
Chesapeake Bay Retreat - "Green Bay"
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
19–24 Jul
19–24 Jul
$1,981 SGD
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for 5 nights
$1,981 SGD for 5 nights
4.89 out of 5 average rating, 53 reviews
4.89 (53)
Top guest favourite
Guest favourite
Barn in Cobbs Creek
The Barn at Pond Point - Riverfront Home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
8–13 Sept
8–13 Sept
$1,878 SGD
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for 5 nights
$1,878 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 136 reviews
4.95 (136)
Top guest favourite
Guest favourite
Tiny home in Deltaville
The Heron's Nest | Tiny Home · Deltaville, VA
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$1,129 SGD
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for 5 nights
$1,129 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
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