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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
12–17 Oct
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4.91 out of 5 average rating, 87 reviews
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Sept
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
Home in Amagansett
Lazy Point Gem w access to Private Beach
3 bedrooms, 3 beds, 1 bathroom
17–22 Aug
New place to stay
Guest favourite
Guest house in Hampton Bays
Tiana Hideaway - Private Hamptons Studio Retreat
1 bathroom
17–22 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Montauk
Sea Ranch At Ditch Plains - Welcome To The Beach
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 6 Sept
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
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, 3 bathrooms
30 Aug – 6 Sept
4.94 out of 5 average rating, 34 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
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, 77 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 127 reviews
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, 8 reviews
Guest favourite
Home in Old Saybrook
Bird Bliss. Our Waterview home &deep water dock.
3 bedrooms, 3 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Cottage in Southampton
Towd Point Beach Cottage w heated pool
3 bedrooms, 4 beds, 2 bathrooms
27 Aug – 1 Sept
4.98 out of 5 average rating, 49 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, 107 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 32 reviews
Superhost
Villa in Southampton
US Golf Open & Ocean View Retreat, Walk to Event
4 bedrooms, 4 beds, 3.5 bathrooms
15–20 Oct
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Guest suite in East Hampton
Hamptons Dream Suite
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 161 reviews