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Search results; Over 1,000 homes in Southold

Guest favorite
Cottage in Southold
Cozy Cottage on the Great Pond near beach.
2 bedrooms, 3 beds, 1.5 private baths
Oct 11 – 16
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4.89 out of 5 average rating, 199 reviews
Top guest favorite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds
Sep 7 – 12
4.96 out of 5 average rating, 23 reviews
Top guest favorite
Home in Greenport
Dream Get Away
2 bedrooms, 2 king beds
Aug 23 – 28
4.94 out of 5 average rating, 291 reviews
Guest favorite
Guesthouse in Hampton Bays
Tiana Hideaway - Private Hamptons Studio Retreat
Aug 30 – Sep 4
5.0 out of 5 average rating, 6 reviews
Home in Old Lyme
Make the "BlueBird" your new summer vacation home!
2 bedrooms, 2 beds
Sep 14 – 19
New place to stay
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds
Aug 31 – Sep 6
Guest favorite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds
Aug 30 – Sep 6
4.94 out of 5 average rating, 34 reviews
Home in Waterford
Salty Breeze: Distant Ocean Views & Porch
3 bedrooms, 5 beds
Aug 30 – Sep 4
New place to stay
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds
Aug 31 – Sep 5
New place to stay
Guest favorite
Apartment in Greenport
Lovely 1st floor of farmhouse, wineries/downtown
1 bedroom, 2 beds
Sep 28 – Oct 3
4.94 out of 5 average rating, 65 reviews
Top guest favorite
Room in Greenport
Greenport Village Private Room w/separate entrance
1 queen bed
Aug 30 – Sep 4
4.97 out of 5 average rating, 155 reviews
Top guest favorite
Room in Clinton
Nautical Nook- 1st Floor - Private 1 Bedroom Suite
1 queen bed
Sep 6 – 11
5.0 out of 5 average rating, 111 reviews
Top guest favorite
Room in Sag Harbor
Sag Harbor Home, Perfect for the Solo Traveler
2 beds
Aug 30 – Sep 4
4.96 out of 5 average rating, 257 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds
Aug 27 – Sep 1
Guest favorite
Apartment in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds
Aug 16 – 21
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Wainscott
Charming Wainscott Cottage
2 bedrooms, 3 beds
Aug 31 – Sep 5
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds
Sep 6 – 11
5.0 out of 5 average rating, 98 reviews
Top guest favorite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds
Sep 8 – 13
5.0 out of 5 average rating, 18 reviews
Top guest favorite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds
Aug 14 – 19
4.93 out of 5 average rating, 86 reviews