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Search results; Over 1,000 homes in Southold

Top guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bathroom
2–7 Aug
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4.95 out of 5 average rating, 146 reviews
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
13–18 Jul
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4.93 out of 5 average rating, 84 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
14–21 Jul
Home in East Hampton
Charming Home for a Perfect Escape
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in East Marion
Waterfront Bungalow w/Private Beach on Peconic Bay
4.88 out of 5 average rating, 42 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–8 Aug
Top guest favourite
Cottage in East Lyme
Beach Cottage!
5.0 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 93 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
Top guest favourite
Home in Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Sag Harbor
Sag Harbor Chic Mid-Century Retreat
4.99 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Old Lyme
Casa Swan
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
Home in Sag Harbor
Sun-Filled, Custom-Designed 5-bedroom Sag Harbor
New place to stay, 5 bedrooms, 7 beds, 3 bathrooms
20–25 Jul
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 10 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
4.97 out of 5 average rating, 71 reviews, 3 bedrooms, 6 beds, 1 bathroom
14–19 Sept
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
Top guest favourite
Home in Old Saybrook
Best of both worlds!
4.92 out of 5 average rating, 110 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
4.98 out of 5 average rating, 48 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul