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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Beach house @ NoFo
3 bedrooms, 5 beds, 2 private bathrooms
31 Aug – 6 Sept
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4.93 out of 5 average rating, 85 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Sept
Guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 10 reviews
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Sept
Home in Old Lyme
Make the "BlueBird" your new summer vacation home!
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 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, 24 reviews
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 6 Sept
4.94 out of 5 average rating, 35 reviews
Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms, 4 beds, 3 bathrooms
25–30 Aug
New place to stay
Top guest favourite
Home in Greenport
Pennington House
3 bedrooms, 3 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 32 reviews
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
New place to stay
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
4.93 out of 5 average rating, 86 reviews
Guest favourite
Villa in East Hampton
Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open
4 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
4.95 out of 5 average rating, 97 reviews
Top guest favourite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in East Hampton
East Hampton Escape | Pool & Private Beach Access
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Top 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, 9 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
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds, 3.5 bathrooms
30 Aug – 6 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms, 3 beds, 1.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 16 reviews