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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Stylish Beach Getaway: pool & walking location
3 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
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4.88 out of 5 average rating, 24 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
Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 4 beds, 3 bathrooms
18–23 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, 3 bathrooms
12–18 Oct
4.89 out of 5 average rating, 133 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
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 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 Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
3 bedrooms, 3 beds, 2 bathrooms
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, 3 bathrooms
11–16 Oct
5.0 out of 5 average rating, 95 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 Southold
Steps from the water! Fall Northfork Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
13–18 Oct
5.0 out of 5 average rating, 20 reviews
Superhost
Home in Old Lyme
Surf Cottage (1 Minute Walk to Private Beach)
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
New place to stay
Top guest favourite
Home in East Marion
New! 6BR, 4.5 Bath, Pool, Hot Tub, Walk to Beach
6 bedrooms, 8 beds, 4.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 25 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 19 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