filters

Search results; Over 1,000 homes in Southold

Photo 1 of 29
Home in Southold
Shelter Bay Cove Waterfront Escape
3 bedrooms, 3 beds, 2 private bathrooms
13–18 Oct
,
4.91 out of 5 average rating, 32 reviews
Photo 1 of 15
Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
New place to stay
Photo 1 of 23
Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
9–14 Oct
4.99 out of 5 average rating, 70 reviews
Photo 1 of 29
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 45 reviews
Photo 1 of 29
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
New place to stay
Photo 1 of 28
Home in Southold
The Shorecrest Beach House
4 bedrooms, 6 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 19
Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.89 out of 5 average rating, 44 reviews
Photo 1 of 29
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
11–16 Oct
4.97 out of 5 average rating, 32 reviews
Photo 1 of 29
Top guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Oct
4.98 out of 5 average rating, 171 reviews
Photo 1 of 29
Home in East Hampton
East Hamptons Modern 8 Bedroom New Construction
8 bedrooms, 8 beds, 6 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 16
Bungalow in Old Lyme
Your Coastal Getaway Awaits in Old Lyme, CT!
3 bedrooms, 3 queen beds, 1.5 bathrooms
4–9 Oct
4.67 out of 5 average rating, 3 reviews
Photo 1 of 21
Top guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.91 out of 5 average rating, 22 reviews
Photo 1 of 29
Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 271 reviews
Photo 1 of 28
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 15
Top guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.92 out of 5 average rating, 119 reviews
Photo 1 of 29
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 131 reviews
Photo 1 of 29
Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 169 reviews
Photo 1 of 29
Top guest favourite
Home in Southold
Country Beach Home!
4 bedrooms, 8 beds, 2.5 bathrooms
6–11 Oct
4.96 out of 5 average rating, 24 reviews