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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Family and Dog Friendly Private Beach
3 bedrooms, 3 beds, 2 private bathrooms
28 Sept – 3 Oct
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5.0 out of 5 average rating, 7 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
New place to stay
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 Sept
Superhost
Home in Shelter Island
Light- filled historic home -walk to water-pool
6 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
Luxe
Villa in East Hampton
Luxe|Pool|BeachCar|Games|Movie|HotTub|Firepit
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 67 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, 109 reviews
Top guest favourite
Home in Clinton
Luxury 5 BR Beachfront Retreat
5 bedrooms, 8 beds, 3 bathrooms
8–13 Sept
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Cottage in Old Lyme
The Solo Shore Cottage | Walk to Beach + Sun Porch
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds, 3 bathrooms
11–16 Oct
5.0 out of 5 average rating, 91 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Mattituck
Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in East Hampton
East Hampton Escape | Pool & Private Beach Access
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 24 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
4.97 out of 5 average rating, 79 reviews
Guest favourite
Home in Old Saybrook
Summertime in Old Saybrook on the Oyster River
5 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Sag Harbor
Updated apartment in historic village home
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 237 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, 128 reviews
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
1–8 Sept
4.94 out of 5 average rating, 35 reviews
Top guest favourite
Home in East Hampton
Serene East Hampton Escape - Stars Forest Sauna
4 bedrooms, 5 beds, 5.5 bathrooms
5–10 Oct
4.99 out of 5 average rating, 152 reviews