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Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Top guest favourite
Guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom
,
·
1 bed
,
·
1 private bathroom
13–18 Sept
13–18 Sept
£1,137
total
Show price breakdown
£1,137 total
,
·
4.94 out of 5 average rating, 158 reviews
4.94 (158)
Top guest favourite
Guest favourite
Flat in Montauk
Lovely large quiet estate on a nature preserve.
3 bedrooms
3 bedrooms
,
·
2 beds
2 beds
20–25 Sept
20–25 Sept
£971
total
Show price breakdown
£971 total
Free cancellation
5.0 out of 5 average rating, 64 reviews
5.0 (64)
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
12–17 Sept
12–17 Sept
£2,886
£2,347
total
Show price breakdown
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Home in Southampton
Vogue Editors Home, Featured Hamptons Mag, Elle D.
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
11–16 Sept
11–16 Sept
£5,562
£3,654
total
Show price breakdown
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
20–25 Sept
20–25 Sept
£1,070
total
Show price breakdown
£1,070 total
Free cancellation
4.97 out of 5 average rating, 29 reviews
4.97 (29)
Top guest favourite
Guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
29 Sept – 4 Oct
29 Sept – 4 Oct
£2,768
£2,469
total
Show price breakdown
Free cancellation
4.96 out of 5 average rating, 179 reviews
4.96 (179)
Guest favourite
Guest favourite
Cottage in Clinton
Cozy cottage near Clinton Marina on CT Shoreline
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
20–25 Sept
20–25 Sept
£977
£881
total
Show price breakdown
Free cancellation
4.95 out of 5 average rating, 93 reviews
4.95 (93)
Top guest favourite
Guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
25–30 Oct
25–30 Oct
£4,164
£3,713
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Top guest favourite
Guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
25–30 Sept
25–30 Sept
£7,447
£6,631
total
Show price breakdown
5.0 out of 5 average rating, 31 reviews
5.0 (31)
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
29 Oct – 3 Nov
29 Oct – 3 Nov
£2,212
£1,981
total
Show price breakdown
Free cancellation
4.98 out of 5 average rating, 170 reviews
4.98 (170)
Luxe
Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
30 Sept – 5 Oct
30 Sept – 5 Oct
£5,079
total
Show price breakdown
£5,079 total
4.99 out of 5 average rating, 68 reviews
4.99 (68)
Home in East Hampton
Simple, Happy Place in East Hampton
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
14–19 Oct
14–19 Oct
£2,219
£1,738
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
14–19 Sept
14–19 Sept
£1,922
total
Show price breakdown
£1,922 total
5.0 out of 5 average rating, 103 reviews
5.0 (103)
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
11–16 Oct
11–16 Oct
£2,679
£2,398
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 94 reviews
5.0 (94)
Top guest favourite
Guest favourite
Home in Amagansett
Ocean views, steps to beach, newly renovated home
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
£9,281
£6,328
total
Show price breakdown
5.0 out of 5 average rating, 22 reviews
5.0 (22)
Top guest favourite
Guest favourite
Home in Old Saybrook
Desirable Fenwood Beach-walk to beach-dogs allowed
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
4–9 Oct
4–9 Oct
£1,954
total
Show price breakdown
£1,954 total
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Guest favourite
Guest favourite
Flat in Greenport
Greenport Condo with Stunning Views & Beach Access
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
20–25 Sept
20–25 Sept
£1,231
total
Show price breakdown
£1,231 total
4.97 out of 5 average rating, 36 reviews
4.97 (36)
Top guest favourite
Guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms
5 bedrooms
,
·
9 beds
9 beds
4–9 Oct
4–9 Oct
£4,458
£3,972
total
Show price breakdown
4.95 out of 5 average rating, 79 reviews
4.95 (79)
Superhost
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
13–18 Sept
13–18 Sept
£7,515
£3,723
total
Show price breakdown
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