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Search results; Over 1,000 homes in Southold

Top guest favorite
Apartment in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bath
Aug 16 – 21
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4.95 out of 5 average rating, 154 reviews
Top guest favorite
Home in Greenport
Dream Get Away
2 bedrooms, 2 king beds, 2.5 baths
Aug 23 – 28
4.94 out of 5 average rating, 291 reviews
Home in Old Lyme
Make the "BlueBird" your new summer vacation home!
2 bedrooms, 2 beds, 2 baths
Sep 14 – 19
New place to stay
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 baths
Aug 31 – Sep 6
Top guest favorite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 baths
Aug 30 – Sep 4
4.95 out of 5 average rating, 55 reviews
Guest favorite
Guesthouse in Hampton Bays
Tiana Hideaway - Private Hamptons Studio Retreat
1 bath
Aug 17 – 22
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Home in Montauk
Dockside 2BR - Marina - Dining - Charter Access Un
2 bedrooms, 3 beds, 1 bath
Sep 7 – 12
4.97 out of 5 average rating, 33 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 baths
Aug 27 – Sep 1
Top guest favorite
Guest suite in Old Saybrook
Cozy Loft Getaway
1 bedroom, 2 beds, 1 bath
Aug 23 – 28
4.98 out of 5 average rating, 110 reviews
Guest favorite
Apartment in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bath
Aug 16 – 21
5.0 out of 5 average rating, 8 reviews
Guest favorite
Apartment in Greenport
Lovely 1st floor of farmhouse, wineries/downtown
1 bedroom, 2 beds, 1 bath
Sep 28 – Oct 3
4.94 out of 5 average rating, 65 reviews
Guest favorite
Home in Mattituck
Lakehouse Getaway North Fork
3 bedrooms, 5 beds, 2 baths
Aug 16 – 21
4.98 out of 5 average rating, 48 reviews
Top guest favorite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 baths
Sep 8 – 13
5.0 out of 5 average rating, 18 reviews
Guest favorite
Home in Cutchogue
Secluded Farmhouse - Studio Apartment Style Unit
1 bedroom, 1 king bed, 1 bath
Aug 30 – Sep 4
4.96 out of 5 average rating, 212 reviews
Guest favorite
Home in East Marion
Charming North Fork escape by the beach
3 bedrooms, 4 beds, 2 baths
Sep 8 – 15
5.0 out of 5 average rating, 12 reviews
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds, 1 bath
Aug 31 – Sep 5
New place to stay
Top guest favorite
Home in Laurel
Peaceful Guesthouse
2 bedrooms, 2 beds, 1.5 baths
Sep 8 – 13
5.0 out of 5 average rating, 35 reviews
Top guest favorite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 baths
Aug 26 – 31
5.0 out of 5 average rating, 101 reviews
Guest favorite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bath
Aug 23 – 28
5.0 out of 5 average rating, 8 reviews