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Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Top guest favourite
Guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom
,
·
1 bed
,
·
1 private bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,707 SGD
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for 5 nights
$1,707 SGD for 5 nights
,
·
4.94 out of 5 average rating, 159 reviews
4.94 (159)
Top guest favourite
Guest favourite
Home in Southold
Steps from the water! Fall Northfork Retreat
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Oct
13–18 Oct
$4,611 SGD
$3,105 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 20 reviews
5.0 (20)
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 Oct
11–16 Oct
$5,382 SGD
$4,774 SGD
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for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Home in Sag Harbor
Comfortable 3 bed in Sag Harbor
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
4 bathrooms
4 bathrooms
14–19 Sept
14–19 Sept
$4,752 SGD
Show price breakdown
for 5 nights
$4,752 SGD for 5 nights
New place to stay
New
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
14–19 Sept
14–19 Sept
$5,961 SGD
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for 5 nights
$5,961 SGD for 5 nights
5.0 out of 5 average rating, 32 reviews
5.0 (32)
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
17–22 Sept
17–22 Sept
$5,168 SGD
$2,951 SGD
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for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Superhost
Superhost
Home in Shelter Island Heights
*New Shelter Island 5Br|Heated Pool+Crescent Beach
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
5 bathrooms
5 bathrooms
15–20 Sept
15–20 Sept
$6,855 SGD
Show price breakdown
for 5 nights
$6,855 SGD for 5 nights
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
$1,127 SGD
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for 5 nights
$1,127 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 25 reviews
4.96 (25)
Top guest favourite
Guest favourite
Home in Southampton
Tranquil Southampton/Sag Harbor 5 Bedroom, Pool
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
18–23 Sept
18–23 Sept
$5,236 SGD
$3,399 SGD
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for 5 nights
4.98 out of 5 average rating, 51 reviews
4.98 (51)
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
$4,023 SGD
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for 5 nights
$4,023 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 69 reviews
4.96 (69)
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
14–19 Sept
14–19 Sept
$5,069 SGD
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for 5 nights
$5,069 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
$1,681 SGD
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for 5 nights
$1,681 SGD for 5 nights
4.92 out of 5 average rating, 514 reviews
4.92 (514)
Guest favourite
Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
12–17 Oct
12–17 Oct
$1,532 SGD
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for 5 nights
$1,532 SGD for 5 nights
4.95 out of 5 average rating, 270 reviews
4.95 (270)
Guest favourite
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
17–22 Sept
17–22 Sept
$8,351 SGD
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for 5 nights
$8,351 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3.5 bathrooms
3.5 bathrooms
21–26 Sept
21–26 Sept
$8,122 SGD
$7,357 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
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
27 Sept – 2 Oct
27 Sept – 2 Oct
$3,240 SGD
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for 5 nights
$3,240 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 60 reviews
4.97 (60)
Top guest favourite
Guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
26 Sept – 1 Oct
26 Sept – 1 Oct
$5,174 SGD
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for 5 nights
$5,174 SGD for 5 nights
4.97 out of 5 average rating, 131 reviews
4.97 (131)
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
$1,432 SGD
$1,261 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 206 reviews
4.98 (206)
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
21–26 Sept
21–26 Sept
$7,952 SGD
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for 5 nights
$7,952 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
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