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Search results; Over 1,000 homes in Southold

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Top guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.92 out of 5 average rating, 96 reviews
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Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds
30 Sept – 7 Oct
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Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds
17–24 Sept
4.95 out of 5 average rating, 37 reviews
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Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds
3–8 Oct
4.96 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Clinton
Luxury 5 BR Beachfront Retreat
5 bedrooms, 8 beds
27 Sept – 2 Oct
4.89 out of 5 average rating, 9 reviews
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Luxe
Home in Montauk
Montauk modern 7-bedroom Heated Pool & hot tub
7 bedrooms, 10 beds
25–30 Oct
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms, 4 beds
25–30 Sept
5.0 out of 5 average rating, 31 reviews
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Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds
20–25 Sept
New place to stay
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Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds
11–16 Oct
4.99 out of 5 average rating, 148 reviews
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Top guest favourite
Home in Amagansett
Bliss by the Ocean!
6 bedrooms, 7 beds
12–17 Oct
4.94 out of 5 average rating, 71 reviews
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Flat in Shelter Island Heights
5 star Waterfront cottage at Dering Harbor Inn.
1 bedroom, 3 beds
20–25 Sept
New place to stay
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Guest favourite
Home in Greenport
Aqua Vista
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 271 reviews
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Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 19 reviews
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Flat in East Hampton
Charming spacious private studio in Springs
1 bedroom, 3 beds
17–22 Sept
5.0 out of 5 average rating, 3 reviews
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Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms, 3 beds
30 Sept – 5 Oct
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Home in Sagaponack
Amazing Home close to Everything -
5 bedrooms, 7 beds
4–9 Oct
4.94 out of 5 average rating, 334 reviews
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Top guest favourite
Home in Sag Harbor
Brick Kiln
4 bedrooms, 4 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds
13–18 Oct
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds
4–9 Oct
4.97 out of 5 average rating, 30 reviews