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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
4–9 Oct
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4.91 out of 5 average rating, 88 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Sept
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Sept
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
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
Home in East Hampton
5 bedroom waterfront on Gardiner's Bay
5 bedrooms, 10 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 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
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
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 Greenport
Pennington House
3 bedrooms, 3 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 32 reviews
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
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
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 Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 6 Sept
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
Guest favourite
Loft in Madison
Walk to Coast! Convenient Cottage in Dtwn Madison
2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 5 reviews