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Search results; Over 1,000 homes in Southold

Descriptions are based on details hosts provide
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
5.0 out of 5 average rating, 92 reviews
Superhost
Home in Southold
Waterfront North Fork Retreat • Sunset & Vineyards
4 bedrooms, 5 beds, 3 bathrooms
16–23 Jul
Top guest favourite
Home in East Marion
Beachfront with kayaks on Gardiner’s Bay
3 bedrooms, 3 beds, 3.5 bathrooms
16–23 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Southold
Peconic Pearl Cottage
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Shelter Island
New build with pool and beach access
3 bedrooms, 5 beds, 3 bathrooms
15–20 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Southold
Private Waterfront Access + Hot Tub + Scenic Yard
3 bedrooms, 5 beds, 2.5 bathrooms
15–21 Jul
5.0 out of 5 average rating, 45 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Greenport
Private beach access near North Fork wineries
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 181 reviews
Top guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
3 bedrooms, 4 beds, 2 bathrooms
16–21 Jul
4.98 out of 5 average rating, 48 reviews
Home in Shelter Island
Quiet street, walking distance to beach
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in East Marion
Heated mineral pool near North Fork wineries
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 29 reviews
Home in Southampton
Waterfront with kayaks and a fire pit
3 bedrooms, 5 beds, 1.5 bathrooms
15–22 Jul
New place to stay
Guest favourite
Home in East Marion
Pool and garden, steps from the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Sag Harbor
Renovated 1880 home near Main St
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 228 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
8–15 Aug
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
4.93 out of 5 average rating, 84 reviews
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 3 reviews