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Search results; Over 1,000 homes in Southold

Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
6–11 Sept
5.0 out of 5 average rating, 98 reviews
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 18 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 Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 24 reviews
Guest favourite
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 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, 78 reviews
Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 60 reviews
Guest favourite
Home in Water Mill
Water Mill Retreat
3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 12 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Sept
Top guest favourite
Room in Greenport
Greenport Village Private Room w/separate entrance
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 155 reviews
Guest favourite
Home in Sag Harbor
Barefoot Bliss | Quiet Family Retreat Heated Pool
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Sept
4.91 out of 5 average rating, 201 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.88 out of 5 average rating, 16 reviews
Top guest favourite
Bungalow in East Hampton
Charming Bungalow on the Bay
2 bedrooms, 7 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 king bed, 1 bathroom
31 Aug – 5 Sept
4.94 out of 5 average rating, 155 reviews
Guest favourite
Home in East Hampton
Walk to village and hidden from the hustle EH home
3 bedrooms, 3 beds, 2 bathrooms
9–15 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms, 4 beds, 2.5 bathrooms
24–30 Oct
4.98 out of 5 average rating, 171 reviews
Room in Southold
The Terry Inn Master Suite
1 bed, 1 bathroom
17–22 Aug
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