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Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Photo 1 of 28
Home in Southold
The Shorecrest Beach House
4 bedrooms
,
·
6 beds
,
·
2 private bathrooms
19–24 Oct
19–24 Oct
£3,647
total
Show price breakdown
£3,647 total
,
·
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
11–16 Oct
11–16 Oct
£2,677
£2,397
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 93 reviews
5.0 (93)
Photo 1 of 29
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
£5,220
total
Show price breakdown
£5,220 total
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Photo 1 of 23
Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
20–25 Sept
20–25 Sept
£2,952
total
Show price breakdown
£2,952 total
Free cancellation
New place to stay
New
Photo 1 of 29
Guest favourite
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
7.5 bathrooms
7.5 bathrooms
11–16 Sept
11–16 Sept
£5,672
£4,137
total
Show price breakdown
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 20
Top guest favourite
Guest favourite
Home in East Lyme
Charming Cottage in Private Oak Grove Beach
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1 bathroom
1 bathroom
8–13 Nov
8–13 Nov
£963
£841
total
Show price breakdown
Free cancellation
4.98 out of 5 average rating, 80 reviews
4.98 (80)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
6–11 Sept
6–11 Sept
£3,443
total
Show price breakdown
£3,443 total
4.97 out of 5 average rating, 129 reviews
4.97 (129)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Guilford
"Red House on the Knoll" at Indian Cove
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
18–23 Sept
18–23 Sept
£2,062
total
Show price breakdown
£2,062 total
Free cancellation
4.99 out of 5 average rating, 177 reviews
4.99 (177)
Photo 1 of 28
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3.5 bathrooms
3.5 bathrooms
12–17 Sept
12–17 Sept
£2,532
total
Show price breakdown
£2,532 total
New place to stay
New
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Sept
20–25 Sept
£1,729
£1,490
total
Show price breakdown
5.0 out of 5 average rating, 103 reviews
5.0 (103)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Old Lyme
Cozy Beach Cottage with short walk to the beach
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
2–7 Sept
2–7 Sept
£2,657
total
Show price breakdown
£2,657 total
4.97 out of 5 average rating, 198 reviews
4.97 (198)
Photo 1 of 24
Top guest favourite
Guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
£2,493
total
Show price breakdown
£2,493 total
5.0 out of 5 average rating, 22 reviews
5.0 (22)
Photo 1 of 29
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
7–14 Sept
7–14 Sept
£3,932
£3,313
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
9–14 Sept
9–14 Sept
£1,668
total
Show price breakdown
£1,668 total
4.97 out of 5 average rating, 146 reviews
4.97 (146)
Photo 1 of 21
Guest favourite
Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
£5,159
total
Show price breakdown
£5,159 total
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
£2,209
total
Show price breakdown
£2,209 total
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Southold
Country Beach Home!
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
2.5 bathrooms
2.5 bathrooms
20–25 Sept
20–25 Sept
£4,442
total
Show price breakdown
£4,442 total
4.95 out of 5 average rating, 22 reviews
4.95 (22)
Photo 1 of 29
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
£3,373
total
Show price breakdown
£3,373 total
New place to stay
New
Photo 1 of 10
Top guest favourite
Guest favourite
Home in Sag Harbor
Sag Harbor home away from home
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
£2,348
total
Show price breakdown
£2,348 total
4.98 out of 5 average rating, 236 reviews
4.98 (236)
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