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Search results; Over 1,000 homes in Southold

Superhost
Home in Old Lyme
Connecticut Beach Home
Business host
12–17 Sept
New place to stay
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
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
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 3 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
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds
12–19 Sept
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
13–18 Sept
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
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
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds
29 Sept – 4 Oct
4.96 out of 5 average rating, 179 reviews
Top guest favourite
Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds
21–26 Sept
4.99 out of 5 average rating, 178 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms
21–26 Sept
5.0 out of 5 average rating, 10 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 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, 25 reviews
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds
14–19 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Montauk
Lovely large quiet estate on a nature preserve.
3 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 65 reviews
Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds
12–17 Sept
5.0 out of 5 average rating, 19 reviews