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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
8–13 Sept
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4.97 out of 5 average rating, 31 reviews
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
4.96 out of 5 average rating, 97 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
15–20 Nov
Home in East Hampton
The Springs House
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
11–18 Aug
Top guest favourite
Home in East Hampton
Hamptons Beach House
5.0 out of 5 average rating, 17 reviews, 4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 10 beds, 2 bathrooms
29 Aug – 3 Sept
Home in Southold
The Shorecrest Beach House
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 2 bathrooms
14–19 Oct
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Superhost
Tent in East Hampton
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
4.86 out of 5 average rating, 56 reviews, 1 bedroom, 3 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Madison
Fabulous pool in beach town!
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Superhost
Home in Clinton
The Blue Mermaid
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
Home in East Hampton
Tranquil Springs Cottage
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Home in East Hampton
Eauclaire Street cozy cottage
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Sag Harbor
Hamptons Retreat | Pool, Hot Tub, Built-in BBQ
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
4.95 out of 5 average rating, 65 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Guest favourite
Home in Peconic
Provence on the North Fork
4.94 out of 5 average rating, 34 reviews, 3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 6 Sept
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
2–7 Oct