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Search results; Over 1,000 homes in Southold

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Guest favourite
Home in Southold
Stylish Beach Getaway: pool & walking location
3 bedrooms, 4 beds, 2 private bathrooms
28 Sept – 3 Oct
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4.88 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Montauk
Oceanfront Home Downtown Montauk
3 bedrooms, 6 beds, 1.5 bathrooms
5–10 Oct
4.91 out of 5 average rating, 34 reviews
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Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms, 4 beds, 3 bathrooms
18–23 Sept
New place to stay
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Top 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, 8 reviews
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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
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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
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Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds, 7.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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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
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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
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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Top guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 64 reviews
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Superhost
Home in Old Lyme
Surf Cottage (1 Minute Walk to Private Beach)
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
New place to stay
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Top guest favourite
Home in East Hampton
Elegant Springs Retreat (New Construction)
4 bedrooms, 3.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 11 reviews
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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
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Home in East Hampton
Secluded Luxury: New Gunite Pool, Walk to Bay
5 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 58 reviews
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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
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Guest favourite
Home in Greenport
Walk to Beach or to Town …
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.88 out of 5 average rating, 43 reviews