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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
16–21 Aug
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4.95 out of 5 average rating, 154 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
6–11 Sept
5.0 out of 5 average rating, 98 reviews
Guest favourite
Home in Cutchogue
Secluded Farmhouse - Studio Apartment Style Unit
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 212 reviews
Top guest favourite
Guest suite in Old Saybrook
Cozy Loft Getaway
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 110 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Laurel
Peaceful Guesthouse
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 77 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms, 4 beds, 2.5 bathrooms
24–30 Oct
4.98 out of 5 average rating, 171 reviews
Guest favourite
Loft in Madison
Walk to Coast! Convenient Cottage in Dtwn Madison
2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 18 reviews
Home in Sag Harbor
Sun-Filled, Custom-Designed 5-bedroom Sag Harbor
5 bedrooms, 7 beds, 3 bathrooms
12–17 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in East Hampton
Walk to village and hidden from the hustle EH home
3 bedrooms, 3 beds, 2 bathrooms
9–15 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 154 reviews
Top guest favourite
Room in East Hampton
Peaceful Suite w/Pool, Hot tub, Private Entry.
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Sag Harbor
Barefoot Bliss | Quiet Family Retreat Heated Pool
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Sept
4.91 out of 5 average rating, 201 reviews