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Search results; Over 1,000 homes in Southold

Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds
11–16 Sept
5.0 out of 5 average rating, 5 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
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, 64 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
13–18 Sept
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds
10–15 Sept
New place to stay
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 19 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 East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds
10–17 Sept
5.0 out of 5 average rating, 13 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
Bungalow in Old Lyme
Your Coastal Getaway Awaits in Old Lyme, CT!
3 bedrooms, 3 queen beds
14–19 Sept
New place to stay
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 4 beds
10–15 Sept
New place to stay
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
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
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds
4–9 Oct
4.95 out of 5 average rating, 79 reviews
Guest favourite
Cottage in Clinton
Cozy cottage near Clinton Marina on CT Shoreline
3 bedrooms, 5 beds
20–25 Sept
4.95 out of 5 average rating, 93 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
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 129 reviews