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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
5–10 Jul
5–10 Jul
$1,793 SGD
Show price breakdown
for 5 nights
$1,793 SGD for 5 nights
,
·
4.94 out of 5 average rating, 147 reviews
4.94 (147)
Top guest favourite
Guest favourite
Home in Greenport
Beach Block Hideaway
5.0 out of 5 average rating, 23 reviews
5.0 (23)
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$2,136 SGD
Show price breakdown
for 5 nights
$2,136 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
4.9 out of 5 average rating, 80 reviews
4.9 (80)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
23–28 Aug
23–28 Aug
$1,840 SGD
$1,679 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
4.9 out of 5 average rating, 196 reviews
4.9 (196)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,614 SGD
Show price breakdown
for 5 nights
$2,614 SGD for 5 nights
Free cancellation
Flat in Southold
Kenney's Beach Loft - Vineyards, Horton Lighthouse
5.0 out of 5 average rating, 4 reviews
5.0 (4)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
20–25 Jul
20–25 Jul
$4,014 SGD
Show price breakdown
for 5 nights
$4,014 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
5.0 out of 5 average rating, 45 reviews
5.0 (45)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–11 Jul
5–11 Jul
$7,922 SGD
$6,094 SGD
Show price breakdown
for 6 nights
Guest favourite
Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
4.94 out of 5 average rating, 144 reviews
4.94 (144)
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$2,106 SGD
Show price breakdown
for 5 nights
$2,106 SGD for 5 nights
Guest favourite
Guest favourite
Home in Southold
Le Petit Cottage, Southold, NY
4.91 out of 5 average rating, 79 reviews
4.91 (79)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Sept
5–10 Sept
$2,190 SGD
Show price breakdown
for 5 nights
$2,190 SGD for 5 nights
Top guest favourite
Guest favourite
Cottage in Southold
Adorable Cottage
4.95 out of 5 average rating, 77 reviews
4.95 (77)
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$3,014 SGD
Show price breakdown
for 5 nights
$3,014 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Southold
Dockside Getaway in Southold NY
4.95 out of 5 average rating, 40 reviews
4.95 (40)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
4–9 Jul
4–9 Jul
$7,903 SGD
Show price breakdown
for 5 nights
$7,903 SGD for 5 nights
Guest favourite
Guest favourite
Home in Southold
Peconic Pearl Cottage
5.0 out of 5 average rating, 5 reviews
5.0 (5)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$4,785 SGD
Show price breakdown
for 5 nights
$4,785 SGD for 5 nights
Guest favourite
Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
4.92 out of 5 average rating, 66 reviews
4.92 (66)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
8–15 Jul
8–15 Jul
$5,925 SGD
$4,885 SGD
Show price breakdown
for 7 nights
Weekly discount
Guest favourite
Guest favourite
Home in Southold
Southold waterfront 4 bed, pool open til October
4.9 out of 5 average rating, 77 reviews
4.9 (77)
,
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4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
24–29 Jul
24–29 Jul
$11,824 SGD
Show price breakdown
for 5 nights
$11,824 SGD for 5 nights
Guest favourite
Guest favourite
Room in Southold
Cozy guest room - quiet getaway - wine country
4.96 out of 5 average rating, 150 reviews
4.96 (150)
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
27 Oct – 1 Nov
27 Oct – 1 Nov
$1,105 SGD
$975 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Home in Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews
5.0 (7)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
19–24 Jul
19–24 Jul
$10,756 SGD
Show price breakdown
for 5 nights
$10,756 SGD for 5 nights
Flat in Southold
1BR Apartment - Beach Access - Wineries, Vineyards
New place to stay
New
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,316 SGD
Show price breakdown
for 5 nights
$2,316 SGD for 5 nights
Guest favourite
Guest favourite
Apartment in Greenport
Beachside Waterview 2Br Condo w/ Pool in Greenport
4.9 out of 5 average rating, 155 reviews
4.9 (155)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$3,569 SGD
$2,978 SGD
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for 5 nights
Guest favourite
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
5.0 out of 5 average rating, 5 reviews
5.0 (5)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
25–30 Jul
25–30 Jul
$5,041 SGD
Show price breakdown
for 5 nights
$5,041 SGD for 5 nights
Guest favourite
Guest favourite
Flat in Southold
Charming North Fork Escape
5.0 out of 5 average rating, 6 reviews
5.0 (6)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,098 SGD
Show price breakdown
for 5 nights
$2,098 SGD for 5 nights
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