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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
18–23 Sept
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4.89 out of 5 average rating, 197 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
13–20 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 Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
1–7 Aug
Home in Laurel
North Fork Luxury Retreat with Exceptional Comfort
New place to stay, 5 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
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
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
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
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
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
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 Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
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 East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 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
Top guest favourite
Home in Westbrook
Home Away From Home
4.99 out of 5 average rating, 84 reviews, 3 bedrooms, 6 beds, 2 bathrooms
20–25 Aug
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
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
Home in Mattituck
3 bed 2 bath sleeps 5 on north fork of Long Island
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept