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
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms
,
·
3 beds
,
·
2 private bathrooms
8–13 Sept
8–13 Sept
$5,036 SGD
Show price breakdown
for 5 nights
$5,036 SGD for 5 nights
,
·
4.97 out of 5 average rating, 31 reviews
4.97 (31)
Guest favourite
Guest favourite
Home in Shelter Island
Shelter Island House: Peaceful Retreat
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
6–11 Aug
6–11 Aug
$8,031 SGD
Show price breakdown
for 5 nights
$8,031 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Superhost
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
24–29 Jul
24–29 Jul
$8,912 SGD
Show price breakdown
for 5 nights
$8,912 SGD for 5 nights
Free cancellation
Home in Southold
Sunset Cottage
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
21–28 Jul
21–28 Jul
$7,318 SGD
Show price breakdown
for 7 nights
$7,318 SGD for 7 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Home in Branford
Adorable Beach House on LI Sound
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,586 SGD
Show price breakdown
for 5 nights
$1,586 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 99 reviews
4.98 (99)
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
3–8 Aug
3–8 Aug
$7,414 SGD
Show price breakdown
for 5 nights
$7,414 SGD for 5 nights
Free cancellation
New place to stay
New
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
19–26 Jul
19–26 Jul
$8,295 SGD
$7,007 SGD
Show price breakdown
for 7 nights
Free cancellation
Guest favourite
Guest favourite
Home in Old Saybrook
Red Bird Waterfront Home. Dock available extra!
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$7,381 SGD
Show price breakdown
for 5 nights
$7,381 SGD for 5 nights
4.94 out of 5 average rating, 35 reviews
4.94 (35)
Top guest favourite
Guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
8–15 Aug
8–15 Aug
$4,225 SGD
Show price breakdown
for 7 nights
$4,225 SGD for 7 nights
Free cancellation
4.99 out of 5 average rating, 74 reviews
4.99 (74)
Guest favourite
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
19–24 Jul
19–24 Jul
$11,723 SGD
Show price breakdown
for 5 nights
$11,723 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Top guest favourite
Guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
9–14 Aug
9–14 Aug
$10,079 SGD
Show price breakdown
for 5 nights
$10,079 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 40 reviews
4.95 (40)
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
9–14 Aug
9–14 Aug
$6,598 SGD
Show price breakdown
for 5 nights
$6,598 SGD for 5 nights
4.94 out of 5 average rating, 54 reviews
4.94 (54)
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms
2 bedrooms
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$4,140 SGD
Show price breakdown
for 5 nights
$4,140 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
22–27 Sept
22–27 Sept
$6,169 SGD
Show price breakdown
for 5 nights
$6,169 SGD for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Guest favourite
Guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
8–13 Aug
8–13 Aug
$1,911 SGD
Show price breakdown
for 5 nights
$1,911 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms
5 bedrooms
,
·
10 beds
10 beds
,
·
2 bathrooms
2 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$9,667 SGD
Show price breakdown
for 5 nights
$9,667 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Home in Sag Harbor
Charming house in Sag Harbor.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
14–19 Sept
14–19 Sept
$4,644 SGD
Show price breakdown
for 5 nights
$4,644 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$2,999 SGD
Show price breakdown
for 5 nights
$2,999 SGD for 5 nights
4.96 out of 5 average rating, 28 reviews
4.96 (28)
Superhost
Superhost
Flat in Mattituck
Vineyard Views: Private Patio and BBQ, Farm Access
1 bedroom
1 bedroom
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
19–24 Jul
19–24 Jul
$3,477 SGD
$2,975 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
1
2
3
4
…
15
