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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
23–28 Aug
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4.9 out of 5 average rating, 82 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
3 bedrooms, 3 beds, 3.5 bathrooms
10–17 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Home in Southold
Beach Front House
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
6–11 Dec
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
11–16 Jul
Guest favourite
Home in Madison
Fabulous pool in beach town!
4 bedrooms, 4 beds, 2.5 bathrooms
10–15 Jul
4.95 out of 5 average rating, 22 reviews
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
4.97 out of 5 average rating, 177 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 37 reviews
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 97 reviews
Top guest favourite
Bungalow in East Hampton
Charming Bungalow on the Bay
2 bedrooms, 7 beds, 1.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds, 3.5 bathrooms
6–11 Jul
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 248 reviews
Top guest favourite
Cottage in Southampton
10 mins from US OPEN Cottage w heated pool
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 47 reviews
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.74 out of 5 average rating, 250 reviews