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Search results; Over 1,000 homes in Southold

Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 private bathrooms
30 Aug – 4 Sept
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4.94 out of 5 average rating, 53 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 37 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
4.97 out of 5 average rating, 29 reviews, 5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 3.5 bathrooms
8–13 Sept
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
10–17 Jul
Top guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
4.99 out of 5 average rating, 144 reviews, 7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
4.96 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 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
27 Jul – 1 Aug
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 Shelter Island
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 92 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
13–20 Jul
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
5.0 out of 5 average rating, 81 reviews, 4 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Top guest favourite
Home in East Hampton
Bay Access Cottage + Pilates Gym
5.0 out of 5 average rating, 65 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
4.97 out of 5 average rating, 114 reviews, 6 bedrooms, 8 beds, 4 bathrooms
8–15 Sept
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
4.95 out of 5 average rating, 63 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
Home in Shelter Island
Captain Don’s Paradise
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Old Lyme
Casa Swan
5.0 out of 5 average rating, 27 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept