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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private bathrooms
27 Jul – 1 Aug
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4.89 out of 5 average rating, 197 reviews
Guest favourite
Home in Old Saybrook
Bird Bliss. Our Waterview home &deep water dock.
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 3 bathrooms
12–17 Jul
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
New place to stay, 5 bedrooms, 7 beds, 2 bathrooms
15–22 Aug
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Mattituck
Lakehouse Getaway North Fork
5.0 out of 5 average rating, 44 reviews, 3 bedrooms, 5 beds, 2 bathrooms
11–16 Jul
Home in Amagansett
Unit 211: Cottage | Ocean View | Striper
2 bedrooms, 1 bathroom
20–25 Sept
Top guest favourite
Home in East Marion
Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
10–17 Jul
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
28 Aug – 2 Sept
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
10–15 Jul
Home in Mattituck
3 bed 2 bath sleeps 5 on north fork of Long Island
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
5.0 out of 5 average rating, 82 reviews, 4 bedrooms, 5 beds, 3 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 Jul
Guest favourite
Home in East Marion
Waterfront Bungalow w/Private Beach on Peconic Bay
4.88 out of 5 average rating, 42 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–8 Aug
Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
4.93 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.91 out of 5 average rating, 93 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
5.0 out of 5 average rating, 90 reviews, 2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
Top guest favourite
Home in Southold
Beach Front House
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul