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
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,616 SGD
Show price breakdown
for 5 nights
$2,616 SGD for 5 nights
,
·
4.9 out of 5 average rating, 196 reviews
4.9 (196)
Top guest favourite
Guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
10–17 Jul
10–17 Jul
$11,527 SGD
Show price breakdown
for 7 nights
$11,527 SGD for 7 nights
Free cancellation
5.0 out of 5 average rating, 25 reviews
5.0 (25)
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms
5 bedrooms
,
·
10 beds
10 beds
12–17 Jul
12–17 Jul
$9,364 SGD
$7,233 SGD
Show price breakdown
for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
16–21 Aug
16–21 Aug
$2,271 SGD
Show price breakdown
for 5 nights
$2,271 SGD for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 15 reviews
4.93 (15)
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
27 Jul – 1 Aug
27 Jul – 1 Aug
$9,517 SGD
Show price breakdown
for 5 nights
$9,517 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
14–19 Aug
14–19 Aug
$3,268 SGD
Show price breakdown
for 5 nights
$3,268 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Top guest favourite
Guest favourite
Home in Southold
Beach Front House
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
19–24 Jul
19–24 Jul
$11,268 SGD
Show price breakdown
for 5 nights
$11,268 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
25–30 Jul
25–30 Jul
$5,017 SGD
Show price breakdown
for 5 nights
$5,017 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Superhost
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
6–11 Dec
6–11 Dec
$3,700 SGD
Show price breakdown
for 5 nights
$3,700 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
12–17 Jul
12–17 Jul
$3,422 SGD
$2,952 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favourite
Guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
9–14 Aug
9–14 Aug
$1,835 SGD
Show price breakdown
for 5 nights
$1,835 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Top guest favourite
Guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
11–16 Oct
11–16 Oct
$3,426 SGD
Show price breakdown
for 5 nights
$3,426 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Top guest favourite
Guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
9–14 Aug
9–14 Aug
$10,354 SGD
Show price breakdown
for 5 nights
$10,354 SGD for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 37 reviews
4.95 (37)
Guest favourite
Guest favourite
Home in Clinton
Vintage Shoreline Cottage with Sandy Beach
10 bedrooms
10 bedrooms
,
·
15 beds
15 beds
9–15 Sept
9–15 Sept
$6,201 SGD
Show price breakdown
for 6 nights
$6,201 SGD for 6 nights
Free cancellation
4.86 out of 5 average rating, 59 reviews
4.86 (59)
Guest favourite
Guest favourite
Home in Southold
Charming Ranch in North Fork
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
15–20 Aug
15–20 Aug
$3,908 SGD
Show price breakdown
for 5 nights
$3,908 SGD for 5 nights
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Top guest favourite
Guest favourite
Flat in Greenport
Newly Renovated 2-BR Apartment
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
26–31 Jul
26–31 Jul
$2,703 SGD
Show price breakdown
for 5 nights
$2,703 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 87 reviews
4.98 (87)
Top guest favourite
Guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
13–18 Sept
13–18 Sept
$2,401 SGD
$1,864 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 54 reviews
5.0 (54)
Top guest favourite
Guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
9–14 Sept
9–14 Sept
$3,883 SGD
Show price breakdown
for 5 nights
$3,883 SGD for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 171 reviews
4.96 (171)
Top guest favourite
Guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
1–6 Aug
1–6 Aug
$11,001 SGD
Show price breakdown
for 5 nights
$11,001 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 82 reviews
5.0 (82)
1
2
3
4
…
15