Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Southold
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Guest favourite
Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms
,
·
3 beds
,
·
1.5 private bathrooms
18–23 Sept
18–23 Sept
$2,347 SGD
Show price breakdown
for 5 nights
$2,347 SGD for 5 nights
,
·
4.89 out of 5 average rating, 197 reviews
4.89 (197)
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
13–20 Jul
13–20 Jul
$8,303 SGD
$7,014 SGD
Show price breakdown
for 7 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews
5.0 (8)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
13–18 Jul
13–18 Jul
$12,191 SGD
Show price breakdown
for 5 nights
$12,191 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
5.0 out of 5 average rating, 12 reviews
5.0 (12)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–7 Aug
1–7 Aug
$4,268 SGD
Show price breakdown
for 6 nights
$4,268 SGD for 6 nights
Free cancellation
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
New place to stay
New
,
·
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
3–8 Aug
3–8 Aug
$7,644 SGD
Show price breakdown
for 5 nights
$7,644 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Home in East Marion
Waterfront Bungalow w/Private Beach on Peconic Bay
4.88 out of 5 average rating, 42 reviews
4.88 (42)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–8 Aug
1–8 Aug
$9,746 SGD
$7,665 SGD
Show price breakdown
for 7 nights
Free cancellation
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 3 reviews
5.0 (3)
,
·
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$9,524 SGD
Show price breakdown
for 5 nights
$9,524 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 26 reviews
5.0 (26)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3.5 bathrooms
3.5 bathrooms
14–21 Jul
14–21 Jul
$11,536 SGD
Show price breakdown
for 7 nights
$11,536 SGD for 7 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 93 reviews
4.91 (93)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
23–28 Jul
23–28 Jul
$7,086 SGD
Show price breakdown
for 5 nights
$7,086 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
4.98 out of 5 average rating, 48 reviews
4.98 (48)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
15–20 Jul
15–20 Jul
$14,842 SGD
Show price breakdown
for 5 nights
$14,842 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Cottage in East Lyme
Beach Cottage!
5.0 out of 5 average rating, 55 reviews
5.0 (55)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$2,435 SGD
$1,817 SGD
Show price breakdown
for 5 nights
Free cancellation
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
$11,276 SGD
Show price breakdown
for 5 nights
$11,276 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Home in Old Lyme
Casa Swan
5.0 out of 5 average rating, 28 reviews
5.0 (28)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
8–13 Aug
8–13 Aug
$1,913 SGD
Show price breakdown
for 5 nights
$1,913 SGD for 5 nights
Pay $0 today
Free cancellation
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews
5.0 (3)
,
·
5 bedrooms
5 bedrooms
,
·
10 beds
10 beds
,
·
2 bathrooms
2 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$11,414 SGD
Show price breakdown
for 5 nights
$11,414 SGD for 5 nights
Free cancellation
Home in Sag Harbor
Sun-Filled, Custom-Designed 5-bedroom Sag Harbor
New place to stay
New
,
·
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
20–25 Jul
20–25 Jul
$30,423 SGD
Show price breakdown
for 5 nights
$30,423 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Westbrook
Home Away From Home
4.99 out of 5 average rating, 84 reviews
4.99 (84)
,
·
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
20–25 Aug
20–25 Aug
$2,736 SGD
Show price breakdown
for 5 nights
$2,736 SGD for 5 nights
Free cancellation
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms
2 bedrooms
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$4,144 SGD
Show price breakdown
for 5 nights
$4,144 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Sag Harbor
Sag Harbor Chic Mid-Century Retreat
4.99 out of 5 average rating, 76 reviews
4.99 (76)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
9–14 Aug
9–14 Aug
$6,761 SGD
Show price breakdown
for 5 nights
$6,761 SGD for 5 nights
Free cancellation
Home in Mattituck
3 bed 2 bath sleeps 5 on north fork of Long Island
5.0 out of 5 average rating, 4 reviews
5.0 (4)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
8–13 Sept
8–13 Sept
$5,100 SGD
Show price breakdown
for 5 nights
$5,100 SGD for 5 nights
Pay $0 today
Free cancellation
1
2
3
4
…
15