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Search results; Over 1,000 homes in Southold

Guest favourite
Flat in Mattituck
Vineyard Views: Private Patio and BBQ, Farm Access
1 bedroom, 2 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Sept
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Sept
Home in Southampton
Luxury Home with Heated Pool
6 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
New place to stay
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 6 Sept
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in Old Lyme
Cozy Beach Cottage with short walk to the beach
4 bedrooms, 5 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 198 reviews
Luxe
Villa in East Hampton
Luxe|Pool|BeachCar|Games|Movie|HotTub|Firepit
3 bedrooms, 3 beds, 3.5 bathrooms
3–8 Sept
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 77 reviews
Guest favourite
Guest house in Hampton Bays
Tiana Hideaway - Private Hamptons Studio Retreat
1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
New place to stay
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 32 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 6 Sept
Top guest favourite
Home in Greenport
Pennington House
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 55 reviews
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Old Saybrook
Bird Bliss. Our Waterview home &deep water dock.
3 bedrooms, 3 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Room in Southold
The Terry Inn Master Suite
1 bed, 1 bathroom
16–21 Aug
Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds, 3.5 bathrooms
30 Aug – 6 Sept
4.96 out of 5 average rating, 25 reviews