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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
Home in Southold
Luxury by the Sea!!
3 bedrooms
,
·
4 beds
,
·
2.5 private bathrooms
3–8 Oct
3–8 Oct
£3,952 total
Show price breakdown
£3,952 total
,
·
4.95 out of 5 average rating, 59 reviews
4.95 (59)
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
1–6 Oct
1–6 Oct
£2,431
£2,024 total
Show price breakdown
+£243 Airbnb credit
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 Oct
11–16 Oct
£3,449
£2,706 total
Show price breakdown
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Photo 1 of 12
Home in Water Mill
Cozy 5-Bed House in The Hamptons, NY
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
4 bathrooms
4 bathrooms
1–6 Oct
1–6 Oct
£2,829 total
Show price breakdown
£2,829 total
Free cancellation
New place to stay
New
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
£7,786 total
Show price breakdown
£7,786 total
4.99 out of 5 average rating, 148 reviews
4.99 (148)
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
£6,622 total
Show price breakdown
£6,622 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 Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
£1,331 total
Show price breakdown
£1,331 total
Free cancellation
4.97 out of 5 average rating, 31 reviews
4.97 (31)
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
£3,930
£1,918 total
Show price breakdown
4.99 out of 5 average rating, 111 reviews
4.99 (111)
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
£6,961
£5,400 total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 40 reviews
5.0 (40)
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
1–6 Oct
1–6 Oct
£5,246
£4,651 total
Show price breakdown
4.99 out of 5 average rating, 70 reviews
4.99 (70)
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
£3,427
£2,990 total
Show price breakdown
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
4–9 Oct
4–9 Oct
£1,625
£1,461 total
Show price breakdown
Free cancellation
4.97 out of 5 average rating, 199 reviews
4.97 (199)
Photo 1 of 6
Top guest favourite
Guest favourite
Room in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
£857
£760 total
Show price breakdown
4.93 out of 5 average rating, 162 reviews
4.93 (162)
Photo 1 of 29
Guest favourite
Guest favourite
Home in East Hampton
Chic & Spacious Designer Home, Heated Pool/Spa
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
17–22 Oct
17–22 Oct
£2,803 total
Show price breakdown
£2,803 total
4.97 out of 5 average rating, 33 reviews
4.97 (33)
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
£1,148 total
Show price breakdown
£1,148 total
4.98 out of 5 average rating, 169 reviews
4.98 (169)
Photo 1 of 29
Superhost
Superhost
Home in Old Lyme
Connecticut Beach Home
Business host
Business host
10–15 Oct
10–15 Oct
£1,637
£1,389 total
Show price breakdown
New place to stay
New
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 29
Top guest favourite
Guest favourite
Home in Old Saybrook
Waterfront Oasis 4Bdr/2b
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
19–24 Oct
19–24 Oct
£2,925
£2,465 total
Show price breakdown
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Photo 1 of 18
Home in Orient
Brand new 4 bedrm 4.5 bath home with pool & beach
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
4.5 bathrooms
4.5 bathrooms
6–11 Oct
6–11 Oct
£9,256 total
Show price breakdown
£9,256 total
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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