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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, 87 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds
13–18 Sept
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds
7–12 Sept
Home in Southampton
Luxury Home with Heated Pool
6 bedrooms, 6 beds
16–21 Aug
New place to stay
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds
4–9 Oct
4.88 out of 5 average rating, 16 reviews
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds
30 Aug – 6 Sept
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds
7–12 Sept
4.99 out of 5 average rating, 77 reviews
Top guest favourite
Home in Old Lyme
Cozy Beach Cottage with short walk to the beach
4 bedrooms, 5 beds
23–28 Aug
4.97 out of 5 average rating, 198 reviews
Luxe
Villa in East Hampton
Luxe|Pool|BeachCar|Games|Movie|HotTub|Firepit
3 bedrooms, 3 beds
3–8 Sept
4.99 out of 5 average rating, 67 reviews
Guest favourite
Guest house in Hampton Bays
Tiana Hideaway - Private Hamptons Studio Retreat
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Greenport
Pennington House
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 31 reviews
Home in Old Lyme
Make the "BlueBird" your new summer vacation home!
2 bedrooms, 2 beds
14–19 Sept
New place to stay
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
2 bedrooms, 4 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 32 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds
31 Aug – 6 Sept
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Old Saybrook
Bird Bliss. Our Waterview home &deep water dock.
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Home in Southold
The Shorecrest Beach House
4 bedrooms, 6 beds
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms, 2 beds
31 Aug – 5 Sept
New place to stay