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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
,
4.91 out of 5 average rating, 87 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
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
Home in Amagansett
Lazy Point Gem w access to Private Beach
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
New place to stay
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, 170 reviews
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 257 reviews
Guest favourite
Guest house in Madison
Charming Cottage is 1 Mile from Town and Beach
1 bedroom, 1 double bed, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 11 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 Laurel
Peaceful Guesthouse
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 35 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
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 East Hampton
Bay Access Cottage + Pilates Gym
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 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
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Niantic
The Beach House (Costa Casa Pelo Mar)
3 bedrooms, 6 beds, 2.5 bathrooms
8–13 Sept
4.99 out of 5 average rating, 112 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 15 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
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 59 reviews