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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
3 bedrooms, 4 beds, 2 private bathrooms
5–10 Sept
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4.91 out of 5 average rating, 70 reviews
Home in Westbrook
Luxe 5,600-Sq-Ft Estate Waterfront + Pool
5 bedrooms, 8 beds, 5.5 bathrooms
7–12 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, 17 reviews
Top guest favourite
Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 177 reviews
Home in Southampton
Luxury Home with Heated Pool
6 bedrooms, 6 beds, 5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
2–7 Sept
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
4.96 out of 5 average rating, 99 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
Room in Southold
The Terry Inn Master Suite
1 bed, 1 bathroom
20–25 Aug
Top guest favourite
Home in Greenport
Pennington House
3 bedrooms, 3 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 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, 35 reviews
Guest favourite
Villa in East Hampton
Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open
4 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
4.95 out of 5 average rating, 97 reviews
Guest favourite
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 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, 56 reviews
Guest favourite
Home in Old Saybrook
Bird Bliss. Our Waterview home &deep water dock.
3 bedrooms, 3 beds, 3 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 9 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
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