Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
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
Gift cards
Log in or sign up
filters
Filters
Price
Price filter
Type of place
Type of place filter
Show map
Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Photo 1 of 29
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms
,
·
3 beds
,
·
2 private bathrooms
13–18 Oct
13–18 Oct
£2,936 total
Show price breakdown
£2,936 total
,
·
4.91 out of 5 average rating, 32 reviews
4.91 (32)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
£8,453
£5,464 total
Show price breakdown
5.0 out of 5 average rating, 22 reviews
5.0 (22)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
17–22 Sept
17–22 Sept
£5,571
£3,915 total
Show price breakdown
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 23
Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
20–25 Sept
20–25 Sept
£2,988 total
Show price breakdown
£2,988 total
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
20–25 Sept
20–25 Sept
£7,168
£4,357 total
Show price breakdown
4.95 out of 5 average rating, 44 reviews
4.95 (44)
Photo 1 of 15
Bungalow in Old Lyme
Your Coastal Getaway Awaits in Old Lyme, CT!
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
27 Sept – 2 Oct
27 Sept – 2 Oct
£1,363
£1,132 total
Show price breakdown
New place to stay
New
Photo 1 of 27
Top guest favourite
Guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
4–9 Oct
4–9 Oct
£4,019 total
Show price breakdown
£4,019 total
4.97 out of 5 average rating, 30 reviews
4.97 (30)
Photo 1 of 28
Home in Southold
The Shorecrest Beach House
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
19–24 Oct
19–24 Oct
£3,692 total
Show price breakdown
£3,692 total
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
12–17 Oct
12–17 Oct
£1,913 total
Show price breakdown
£1,913 total
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
30 Sept – 5 Oct
30 Sept – 5 Oct
£1,307 total
Show price breakdown
£1,307 total
Free cancellation
4.97 out of 5 average rating, 31 reviews
4.97 (31)
Photo 1 of 14
Guest favourite
Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
12–18 Oct
12–18 Oct
£1,930
£1,677 total
Show price breakdown
4.89 out of 5 average rating, 133 reviews
4.89 (133)
Photo 1 of 29
Superhost
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
18–23 Sept
18–23 Sept
£2,461
£1,595 total
Show price breakdown
New place to stay
New
Photo 1 of 21
Top guest favourite
Guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
25–30 Sept
25–30 Sept
£7,536
£6,711 total
Show price breakdown
5.0 out of 5 average rating, 31 reviews
5.0 (31)
Photo 1 of 29
Guest favourite
Guest favourite
Villa in East Hampton
Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
£3,736
£3,293 total
Show price breakdown
4.95 out of 5 average rating, 100 reviews
4.95 (100)
Photo 1 of 11
Top guest favourite
Guest favourite
Flat in Montauk
Lovely large quiet estate on a nature preserve.
3 bedrooms
3 bedrooms
,
·
2 beds
2 beds
20–25 Sept
20–25 Sept
£982 total
Show price breakdown
£982 total
5.0 out of 5 average rating, 65 reviews
5.0 (65)
Photo 1 of 29
Home in Wainscott
Private, Charming, Lovely Farmhouse, 1 mi to ocean
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
19–24 Oct
19–24 Oct
£2,694 total
Show price breakdown
£2,694 total
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in East Hampton
Beautiful east hampton cottage by the bay
4 bedrooms
4 bedrooms
,
·
2 queen beds
2 queen beds
5–10 Oct
5–10 Oct
£3,316
£2,892 total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Photo 1 of 29
Superhost
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
20–25 Sept
20–25 Sept
£7,586
£3,618 total
Show price breakdown
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms
7 bedrooms
,
·
10 beds
10 beds
11–16 Oct
11–16 Oct
£7,790 total
Show price breakdown
£7,790 total
4.99 out of 5 average rating, 148 reviews
4.99 (148)
1
2
3
4
…
15