filters

Search results; Over 1,000 homes in Southold

Photo 1 of 12
Top guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
,
4.92 out of 5 average rating, 96 reviews
Photo 1 of 29
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
Photo 1 of 29
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms, 3 beds, 3 bathrooms
18–25 Sept
4.95 out of 5 average rating, 37 reviews
Photo 1 of 29
Top guest favourite
Home in East Hampton
Beautiful east hampton cottage by the bay
4 bedrooms, 2 queen beds, 2.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 16 reviews
Photo 1 of 29
Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 18 reviews
Photo 1 of 29
Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 148 reviews
Photo 1 of 28
Top guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
19–26 Sept
5.0 out of 5 average rating, 14 reviews
Photo 1 of 21
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
Photo 1 of 29
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
6–11 Nov
4.75 out of 5 average rating, 260 reviews
Photo 1 of 27
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
4.93 out of 5 average rating, 45 reviews
Photo 1 of 23
Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Home in Amagansett
Bliss by the Ocean!
6 bedrooms, 7 beds, 5.5 bathrooms
12–17 Oct
4.94 out of 5 average rating, 71 reviews
Photo 1 of 29
Luxe
Home in Montauk
Montauk modern 7-bedroom Heated Pool & hot tub
7 bedrooms, 10 beds, 5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 40 reviews
Photo 1 of 29
Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 24 reviews
Photo 1 of 29
Top guest favourite
Home in Clinton
Luxury 5 BR Beachfront Retreat
5 bedrooms, 8 beds, 3 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 9 reviews
Photo 1 of 29
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 131 reviews
Photo 1 of 29
Top guest favourite
Home in Sag Harbor
Brick Kiln
4 bedrooms, 4 beds, 3.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 24 reviews