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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 Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
15–20 Aug
New place to stay
Superhost
Home in Clinton
Beach house with a patio and BBQ
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Jul
Home in Shelter Island Heights
Century-old shingle house on the creek
4 bedrooms, 5 beds, 3.5 bathrooms
15–22 Jul
Home in Laurel
Bright North Fork home with a fireplace
5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
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
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 7 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
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 5 reviews
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
Home in East Hampton
Tranquil Springs Cottage
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 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 East Hampton
5 bedroom waterfront 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
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 Westhampton Beach
Pool and fire pit near the beach
7 bedrooms, 8 beds, 5 bathrooms
26–31 Jul
New place to stay
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
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