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Search results; Over 1,000 homes in Southold

Guest favourite
Home in Southold
Le Petit Cottage, Southold, NY
2 bedrooms, 3 beds, 1 private bathroom
10–15 Oct
,
4.89 out of 5 average rating, 90 reviews
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms, 7 beds
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
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
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Old Lyme
Casa Swan
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 33 reviews
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
Top guest favourite
Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms, 5 beds
21–26 Sept
4.99 out of 5 average rating, 178 reviews
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
20–25 Sept
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Home in Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms, 4 beds
12–18 Oct
4.89 out of 5 average rating, 133 reviews
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
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
2 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
3 bedrooms, 3 beds
29 Oct – 3 Nov
4.98 out of 5 average rating, 170 reviews
Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds
20–25 Sept
New place to stay
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds
29 Sept – 4 Oct
4.96 out of 5 average rating, 179 reviews
Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds
10–15 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Montauk
Lovely large quiet estate on a nature preserve.
3 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms, 5 beds
11–16 Oct
5.0 out of 5 average rating, 94 reviews