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Search results; Over 1,000 homes in Southold

Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 bed, 1 private bathroom
3–8 Oct
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4.94 out of 5 average rating, 159 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, 8 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 Shelter Island Heights
*New Shelter Island 5Br|Heated Pool+Crescent Beach
5 bedrooms, 6 beds, 5 bathrooms
15–20 Sept
Top guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 206 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
Home in Southold
Beautiful waterfront 3 bedroom home in Southold
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Sag Harbor
Charming Cottage in Historic Sag Harbor
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 79 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 reviews
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
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in Shelter Island
Superb Shelter Island 4 bed Designer with a Pool
3 bedrooms, 4 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 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
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 514 reviews
Top guest favourite
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms, 8 beds, 3 bathrooms
21–26 Sept
5.0 out of 5 average rating, 6 reviews
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
Top guest favourite
Home in Southampton
Tranquil Southampton/Sag Harbor 5 Bedroom, Pool
5 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 60 reviews
Top guest favourite
Home in Southold
NoFo Family Beach House — Walk To Private Beach
4 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 34 reviews