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Search results; Over 1,000 homes in Southold

Superhost
Home in Old Lyme
Connecticut Beach Home
Business host
13–18 Sept
New place to stay
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds
20–25 Sept
New place to stay
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 Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds
12–17 Oct
5.0 out of 5 average rating, 19 reviews
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds
30 Sept – 7 Oct
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
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 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, 170 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, 7 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms, 3 beds
17–22 Sept
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
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 4 beds
18–23 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
Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Village 3 Bedroom Gem
3 bedrooms, 3 beds
11–16 Oct
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds
11–16 Oct
4.99 out of 5 average rating, 147 reviews