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Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Photo 1 of 12
Top guest favourite
Guest favourite
Guest house in Southold
Southold- Adorable 1 Bedroom Cottage
1 bedroom
,
·
1 bed
,
·
1 private bathroom
4–9 Oct
4–9 Oct
£1,053
£811 total
Show price breakdown
,
·
4.92 out of 5 average rating, 96 reviews
4.92 (96)
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
5–10 Oct
5–10 Oct
£2,602 total
Show price breakdown
£2,602 total
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 Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
£9,551
£5,460 total
Show price breakdown
5.0 out of 5 average rating, 22 reviews
5.0 (22)
Photo 1 of 27
Top guest favourite
Guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
4–9 Oct
4–9 Oct
£4,015 total
Show price breakdown
£4,015 total
4.97 out of 5 average rating, 30 reviews
4.97 (30)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
£4,133
£3,122 total
Show price breakdown
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Photo 1 of 29
Home in Wainscott
Private, Charming, Lovely Farmhouse, 1 mi to ocean
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
19–24 Oct
19–24 Oct
£2,692 total
Show price breakdown
£2,692 total
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 14
Guest favourite
Guest favourite
Home in East Hampton
4 BD w/ Heated Pool in E Hampton, Fully Furnished
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
12–18 Oct
12–18 Oct
£1,919
£1,606 total
Show price breakdown
4.89 out of 5 average rating, 133 reviews
4.89 (133)
Photo 1 of 29
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
4.5 bathrooms
4.5 bathrooms
30 Sept – 7 Oct
30 Sept – 7 Oct
£21,122
£18,723 total
Show price breakdown
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Sept
20–25 Sept
£4,109 total
Show price breakdown
£4,109 total
4.96 out of 5 average rating, 45 reviews
4.96 (45)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms
7 bedrooms
,
·
10 beds
10 beds
,
·
8.5 bathrooms
8.5 bathrooms
11–16 Oct
11–16 Oct
£7,783 total
Show price breakdown
£7,783 total
4.99 out of 5 average rating, 148 reviews
4.99 (148)
Photo 1 of 29
Superhost
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
£3,537 total
Show price breakdown
£3,537 total
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Greenport
Luxurious Fully Renovated 1880's Farmhouse
8 bedrooms
8 bedrooms
,
·
12 beds
12 beds
,
·
8.5 bathrooms
8.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
£19,421 total
Show price breakdown
£19,421 total
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in East Marion
New! 6BR, 4.5 Bath, Pool, Hot Tub, Walk to Beach
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
4.5 bathrooms
4.5 bathrooms
25–30 Oct
25–30 Oct
£6,004 total
Show price breakdown
£6,004 total
Free cancellation
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Photo 1 of 15
Top guest favourite
Guest favourite
Home in Old Saybrook
Best of both worlds!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
12–17 Oct
12–17 Oct
£1,353 total
Show price breakdown
£1,353 total
Free cancellation
4.92 out of 5 average rating, 119 reviews
4.92 (119)
Photo 1 of 29
Superhost
Superhost
Home in Old Saybrook
Oceanside retreat Sleeps 8 3bds~3bths
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
23–28 Sept
23–28 Sept
£2,462
£1,622 total
Show price breakdown
New place to stay
New
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Sag Harbor
Relax into Coastal Life at a Sun-Drenched Sag Harbor Home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
29 Oct – 3 Nov
29 Oct – 3 Nov
£2,232
£2,004 total
Show price breakdown
Free cancellation
4.98 out of 5 average rating, 171 reviews
4.98 (171)
Photo 1 of 21
Top guest favourite
Guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3.5 bathrooms
3.5 bathrooms
25–30 Sept
25–30 Sept
£7,530
£6,705 total
Show price breakdown
5.0 out of 5 average rating, 31 reviews
5.0 (31)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms
5 bedrooms
,
·
9 beds
9 beds
,
·
3.5 bathrooms
3.5 bathrooms
3–8 Oct
3–8 Oct
£6,359 total
Show price breakdown
£6,359 total
4.96 out of 5 average rating, 27 reviews
4.96 (27)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
30 Sept – 5 Oct
30 Sept – 5 Oct
£1,208 total
Show price breakdown
£1,208 total
Free cancellation
4.97 out of 5 average rating, 31 reviews
4.97 (31)
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