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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
3 bedrooms, 4 beds, 2 private bathrooms
15–22 Aug
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4.92 out of 5 average rating, 66 reviews
Guest favourite
Home in Old Saybrook
Bird Bliss. Our Waterview home &deep water dock.
3 bedrooms, 3 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 5 reviews
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
3 bedrooms, 3 beds, 3.5 bathrooms
10–17 Jul
5.0 out of 5 average rating, 25 reviews
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 6 reviews
Home in Mattituck
3 bed 2 bath sleeps 5 on north fork of Long Island
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Home in East Hampton
Tranquil Springs Cottage
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 82 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 15 reviews
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
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
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 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
Home in Sag Harbor
Sun-Filled, Custom-Designed 5-bedroom Sag Harbor
5 bedrooms, 7 beds, 3 bathrooms
17–22 Jul
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
18–24 Sept
4.98 out of 5 average rating, 166 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
5.0 out of 5 average rating, 91 reviews
Top guest favourite
Home in East Hampton
Idyllic Designer Sunny Cottage StepsToBeach 1.2 ac
3 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
5.0 out of 5 average rating, 18 reviews
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
6–11 Dec