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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Cutchogue
North Fork Paradise
4 bedrooms, 5 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 11 reviews
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
New place to stay
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
11–16 Oct
5.0 out of 5 average rating, 102 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
Top guest favourite
Home in Sag Harbor
Sag Harbor Charming Forest Home
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.97 out of 5 average rating, 60 reviews
Home in Sag Harbor
Comfortable 3 bed in Sag Harbor
3 bedrooms, 3 beds, 4 bathrooms
11–16 Sept
New place to stay
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Cutchogue
Sunny Harbor Suite
1 bedroom, 1 queen bed, 1 bathroom
3–8 Nov
4.96 out of 5 average rating, 25 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 Southold
NoFo Family Beach House — Walk To Private Beach
4 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 34 reviews
Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Sept
4.95 out of 5 average rating, 58 reviews
Guest favourite
Villa in Shelter Island
Superb Shelter Island 4 bed Designer with a Pool
3 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
5.0 out of 5 average rating, 7 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
Home in Greenport
Little House on Center Street
2 bedrooms, 2 queen beds, 1.5 bathrooms
9–14 Sept
New place to stay
Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 270 reviews