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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Stylish Beach Getaway: pool & walking location
3 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
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4.88 out of 5 average rating, 24 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Cottage in Clinton
Cozy cottage near Clinton Marina on CT Shoreline
3 bedrooms, 5 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 93 reviews
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in East Hampton
Secluded Luxury: New Gunite Pool, Walk to Bay
5 bedrooms, 5 beds, 3 bathrooms
10–15 Sept
5.0 out of 5 average rating, 57 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, 10 reviews
Guest favourite
Home in East Hampton
Chic & Spacious Designer Home, Heated Pool/Spa
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.99 out of 5 average rating, 178 reviews
Bungalow in Old Lyme
Your Coastal Getaway Awaits in Old Lyme, CT!
3 bedrooms, 3 queen beds, 1.5 bathrooms
14–19 Sept
New place to stay
Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds, 3.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 79 reviews
Top guest favourite
Home in Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms, 7 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 44 reviews
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms, 4 beds, 3.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.89 out of 5 average rating, 133 reviews
Top guest favourite
Flat in Montauk
Lovely large quiet estate on a nature preserve.
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 64 reviews