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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
,
4.91 out of 5 average rating, 87 reviews
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in East Hampton
Hamptons Beach House
4 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 17 reviews
Home in East Hampton
Eauclaire Street cozy cottage
3 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
New place to stay
Superhost
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
New place to stay
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, 76 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 160 reviews
Superhost
Tent in East Hampton
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.86 out of 5 average rating, 56 reviews
Top guest favourite
Home in Greenport
The North Star: Greenport Waterview Beach Getaway
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 66 reviews
Top guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 55 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 East Hampton
The Springs House
4 bedrooms, 5 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Old Lyme
Cozy Beach Cottage with short walk to the beach
4 bedrooms, 5 beds, 1.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 198 reviews
Top guest favourite
Home in Branford
Adorable Beach House on LI Sound
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 105 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, 34 reviews