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Search results; Over 1,000 homes in Southold

Top guest favourite
Room in Southold
Vine + Sand Southold, NY's Newest B&B-Room 2
1 bedroom, 1 bed, 1 private bathroom
28 Sept – 3 Oct
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5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
20–25 Sept
4.95 out of 5 average rating, 44 reviews
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds
17–22 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 4 beds
18–23 Sept
New place to stay
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds
30 Sept – 5 Oct
4.99 out of 5 average rating, 69 reviews
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds
12–17 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms
22–27 Sept
5.0 out of 5 average rating, 11 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds
21–26 Sept
New place to stay
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Home in East Marion
New! 6BR, 4.5 Bath, Pool, Hot Tub, Walk to Beach
6 bedrooms, 8 beds
25–30 Oct
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms, 4 beds
12–18 Oct
4.89 out of 5 average rating, 133 reviews
Top guest favourite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
3 bedrooms, 3 beds
29 Oct – 3 Nov
4.98 out of 5 average rating, 171 reviews
Top guest favourite
Home in Greenport
Pennington House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds
11–16 Oct
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds
13–18 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms, 4 beds
25–30 Sept
5.0 out of 5 average rating, 31 reviews
Superhost
Home in Old Lyme
Surf Cottage (1 Minute Walk to Private Beach)
2 bedrooms, 3 beds
26 Sept – 1 Oct
New place to stay