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Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Guest favourite
Guest favourite
Home in Southold
Stylish Beach Getaway: pool & walking location
3 bedrooms
,
·
4 beds
,
·
2 private bathrooms
13–18 Sept
13–18 Sept
$5,076 SGD
Show price breakdown
for 5 nights
$5,076 SGD for 5 nights
,
·
4.88 out of 5 average rating, 24 reviews
4.88 (24)
Home in Sag Harbor
Comfortable 3 bed in Sag Harbor
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
4 bathrooms
4 bathrooms
11–16 Sept
11–16 Sept
$4,756 SGD
Show price breakdown
for 5 nights
$4,756 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
12–17 Sept
12–17 Sept
$7,958 SGD
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for 5 nights
$7,958 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Home in Sag Harbor
Sag Harbor Charming Forest Home
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
21–26 Sept
21–26 Sept
$6,284 SGD
$5,385 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
11–16 Sept
11–16 Sept
$5,073 SGD
Show price breakdown
for 5 nights
$5,073 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Home in Cutchogue
Sunny Harbor Suite
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
3–8 Nov
3–8 Nov
$1,128 SGD
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for 5 nights
$1,128 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 25 reviews
4.96 (25)
Guest favourite
Guest favourite
Villa in Shelter Island
Superb Shelter Island 4 bed Designer with a Pool
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
12–17 Sept
12–17 Sept
$3,845 SGD
$2,355 SGD
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for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$1,433 SGD
$1,262 SGD
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for 5 nights
Free cancellation
4.98 out of 5 average rating, 205 reviews
4.98 (205)
Guest favourite
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
7.5 bathrooms
7.5 bathrooms
11–16 Sept
11–16 Sept
$8,796 SGD
$5,524 SGD
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for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favourite
Guest favourite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$1,682 SGD
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for 5 nights
$1,682 SGD for 5 nights
4.92 out of 5 average rating, 514 reviews
4.92 (514)
Top guest favourite
Guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
16–21 Sept
16–21 Sept
$6,105 SGD
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for 5 nights
$6,105 SGD for 5 nights
4.95 out of 5 average rating, 58 reviews
4.95 (58)
Guest favourite
Guest favourite
Home in Cutchogue
Just renovated! North Fork life: pool, beach, wine
4 bedrooms
4 bedrooms
,
·
4 queen beds
4 queen beds
,
·
5 bathrooms
5 bathrooms
13–19 Sept
13–19 Sept
$4,845 SGD
Show price breakdown
for 6 nights
$4,845 SGD for 6 nights
5.0 out of 5 average rating, 25 reviews
5.0 (25)
Guest favourite
Guest favourite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
11–16 Sept
11–16 Sept
$5,577 SGD
$5,123 SGD
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for 5 nights
Extended stay discount
5.0 out of 5 average rating, 45 reviews
5.0 (45)
Top guest favourite
Guest favourite
Cottage in Sag Harbor
Charming Cottage in Historic Sag Harbor
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
17–22 Oct
17–22 Oct
$1,861 SGD
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for 5 nights
$1,861 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 78 reviews
5.0 (78)
Top guest favourite
Guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
24–29 Sept
24–29 Sept
$3,403 SGD
Show price breakdown
for 5 nights
$3,403 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 60 reviews
4.97 (60)
Top guest favourite
Guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26–31 Oct
26–31 Oct
$4,026 SGD
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for 5 nights
$4,026 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 69 reviews
4.96 (69)
Top guest favourite
Guest favourite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
$4,955 SGD
$4,365 SGD
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for 5 nights
5.0 out of 5 average rating, 34 reviews
5.0 (34)
Top guest favourite
Guest favourite
Home in Southold
Beautiful waterfront 3 bedroom home in Southold
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
$4,777 SGD
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for 5 nights
$4,777 SGD for 5 nights
5.0 out of 5 average rating, 32 reviews
5.0 (32)
Top guest favourite
Guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
4 bathrooms
4 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$9,777 SGD
$8,591 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 114 reviews
4.97 (114)
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