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Search results; Over 1,000 homes in Southold

Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
12–17 Oct
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4.91 out of 5 average rating, 87 reviews
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, 23 reviews
Guest favourite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 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
Top guest favourite
Guest suite in Old Saybrook
Cozy Loft Getaway
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 110 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
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, 97 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
Top guest favourite
Home in Laurel
Peaceful Guesthouse
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Cutchogue
Secluded Farmhouse - Studio Apartment Style Unit
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 212 reviews
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, 7 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
Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 17 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
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Montauk
Renovated Oceanfront Montauk Studio Retreat
1 bedroom, 2 beds, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Mattituck
Mattinook, a home by the beach!
3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 6 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
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 154 reviews