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Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Photo 1 of 29
Top guest favourite
Guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom
,
·
1 bed
,
·
1 private bathroom
3–8 Oct
3–8 Oct
£884 total
Show price breakdown
£884 total
,
·
4.94 out of 5 average rating, 159 reviews
4.94 (159)
Photo 1 of 15
Featured hotel
Featured hotel
Hotel in Greenport
Oyster Estate, Classic king
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
£1,802
£1,501 total
Show price breakdown
+£180 Airbnb credit
New place to stay
New
Photo 1 of 26
Featured hotel
Featured hotel
Hotel in Bridgehampton
A Room at the Beach, Bay twin room
1 bedroom
1 bedroom
,
·
2 single beds
2 single beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
£1,562 total
Show price breakdown
£1,562 total
+£184 Airbnb credit
Photo 1 of 20
Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
1–6 Oct
1–6 Oct
£4,265
£1,478 total
Show price breakdown
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
£7,813 total
Show price breakdown
£7,813 total
4.99 out of 5 average rating, 148 reviews
4.99 (148)
Photo 1 of 10
Superhost
Superhost
Cottage in East Hampton
Storybook Cottage Seconds to East Hampton Village
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
2–7 Oct
2–7 Oct
£2,265 total
Show price breakdown
£2,265 total
5.0 out of 5 average rating, 57 reviews
5.0 (57)
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
1–6 Oct
1–6 Oct
£6,645 total
Show price breakdown
£6,645 total
Free cancellation
4.96 out of 5 average rating, 45 reviews
4.96 (45)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in East Hampton
Amagansett Farmhouse Retreat - Pool Through Oct.
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
19–24 Oct
19–24 Oct
£3,943
£1,924 total
Show price breakdown
4.99 out of 5 average rating, 111 reviews
4.99 (111)
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
11–16 Oct
11–16 Oct
£1,504 total
Show price breakdown
£1,504 total
Free cancellation
4.97 out of 5 average rating, 32 reviews
4.97 (32)
Photo 1 of 29
Luxe
Luxe
Home in Montauk
Montauk modern 7-bedroom Heated Pool & hot tub
7 bedrooms
7 bedrooms
,
·
10 beds
10 beds
,
·
5 bathrooms
5 bathrooms
25–30 Oct
25–30 Oct
£6,977
£5,419 total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 41 reviews
5.0 (41)
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
1–6 Oct
1–6 Oct
£3,439
£3,000 total
Show price breakdown
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Superhost
Superhost
Home in Old Lyme
Connecticut Beach Home
Business host
Business host
10–15 Oct
10–15 Oct
£1,649
£1,399 total
Show price breakdown
New place to stay
New
Photo 1 of 24
Top guest favourite
Guest favourite
Home in Montauk
Oceanfront Home Downtown Montauk
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Oct
25–30 Oct
£7,353
£6,465 total
Show price breakdown
4.91 out of 5 average rating, 35 reviews
4.91 (35)
Photo 1 of 29
Luxe
Luxe
Villa in East Hampton
Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3.5 bathrooms
3.5 bathrooms
9–14 Oct
9–14 Oct
£5,200
£3,596 total
Show price breakdown
4.99 out of 5 average rating, 70 reviews
4.99 (70)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Peconic
Provence on the North Fork
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
1–8 Oct
1–8 Oct
£12,777 total
Show price breakdown
£12,777 total
Free cancellation
4.95 out of 5 average rating, 37 reviews
4.95 (37)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
£1,164 total
Show price breakdown
£1,164 total
4.98 out of 5 average rating, 169 reviews
4.98 (169)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in East Lyme
Beach Cottage!
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
£1,115
£995 total
Show price breakdown
5.0 out of 5 average rating, 64 reviews
5.0 (64)
Photo 1 of 13
Guest favourite
Guest favourite
Home in Westbrook
Cottage on the beach
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
19–24 Oct
19–24 Oct
£1,660 total
Show price breakdown
£1,660 total
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 6
Top guest favourite
Guest favourite
Room in Greenport
The Wells House: The Captain’s Quarters 1bed1bath
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
10–15 Nov
10–15 Nov
£1,550 total
Show price breakdown
£1,550 total
Free cancellation
4.99 out of 5 average rating, 82 reviews
4.99 (82)
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