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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
5–10 Sept
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4.97 out of 5 average rating, 31 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
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
3 bedrooms, 5 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms, 4 beds, 2.5 bathrooms
18–24 Sept
4.98 out of 5 average rating, 166 reviews
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Southold
Beach Front House
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
13–20 Jul
5.0 out of 5 average rating, 26 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 Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 98 reviews
Top guest favourite
Home in Westbrook
Home Away From Home
3 bedrooms, 6 beds, 2 bathrooms
20–25 Aug
4.99 out of 5 average rating, 84 reviews
Top guest favourite
Home in East Hampton
Idyllic Designer Sunny Cottage StepsToBeach 1.2 ac
3 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Madison
Fabulous pool in beach town!
4 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Chic Mid-Century Retreat
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 76 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Home in Mattituck
3 bed 2 bath sleeps 5 on north fork of Long Island
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
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
15–20 Jul
4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in East Marion
North Fork Coastal living in East Marion
4 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.88 out of 5 average rating, 99 reviews