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Search results; Over 1,000 homes in Southold

Descriptions are based on details hosts provide
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
15–20 Jul
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Clinton
Beach house with a patio and BBQ
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
15–22 Jul
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
Guest favourite
Home in Greenport
Bay view with a heated saltwater pool
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 10 reviews
Home in East Hampton
Private beach access and a fire pit
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Old Lyme
Fire pit, outdoor shower, walk to beach
2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 5 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
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
16–23 Jul
5.0 out of 5 average rating, 26 reviews
Home in East Hampton
Architect-designed beach house on Gardiner’s Bay
5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in East Marion
Waterfront Bungalow w/Private Beach on Peconic Bay
3 bedrooms, 4 beds, 1.5 bathrooms
1–8 Aug
4.88 out of 5 average rating, 42 reviews
Home in Westhampton Beach
Pool and fire pit near the beach
7 bedrooms, 8 beds, 5 bathrooms
26–31 Jul
New place to stay
Top guest favourite
Home in Southold
Exclusive beach access and sunset views
4 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 7 reviews
Home in East Hampton
Finished basement, fire pit, and private backyard
5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Home in Sag Harbor
Sun-Filled, Custom-Designed 5-bedroom Sag Harbor
5 bedrooms, 7 beds, 3 bathrooms
20–25 Jul
New place to stay
Top guest favourite
Home in East Hampton
New build with a pool and fire pit
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
1–7 Aug
5.0 out of 5 average rating, 12 reviews