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Search results; Over 1,000 homes in Southold

Guest favourite
Cottage in Southold
Bordeaux meets Côte d’Azur—1763 Historic Farmhouse
3 bedrooms, 4 beds, 2 private bathrooms
26–31 Oct
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4.91 out of 5 average rating, 70 reviews
Superhost
Home in Old Lyme
Connecticut Beach Home
Business host
13–18 Sept
New place to stay
Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds
20–25 Sept
New place to stay
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
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 5 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
Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms, 3 beds
20–25 Sept
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds
30 Sept – 7 Oct
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
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, 95 reviews
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, 23 reviews
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, 147 reviews
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds
12–17 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds
4–9 Oct
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds
20–25 Sept
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms, 8 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Home in East Hampton
Secluded Luxury: New Gunite Pool, Walk to Bay
5 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 57 reviews
Superhost
Home in East Hampton
Contemporary house East Hampton with heated pool
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews