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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
3 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
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4.91 out of 5 average rating, 70 reviews
Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
New place to stay
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Montauk
Lovely large quiet estate on a nature preserve.
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 65 reviews
Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.89 out of 5 average rating, 133 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
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, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
3 bedrooms, 6 beds, 1 bathroom
8–13 Nov
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.99 out of 5 average rating, 178 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds, 3 bathrooms
11–16 Oct
5.0 out of 5 average rating, 95 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
New place to stay
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
11–18 Sept
5.0 out of 5 average rating, 13 reviews
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds, 1 bathroom
14–19 Oct
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
29 Sept – 4 Oct
4.96 out of 5 average rating, 179 reviews
Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 23 reviews