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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 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
4.95 out of 5 average rating, 44 reviews
4.95 (44)
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 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
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
Free cancellation
New place to stay
New
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 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
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
20–25 Sept
20–25 Sept
£6,678
£3,203 total
Show price breakdown
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
20–25 Sept
20–25 Sept
£3,412 total
Show price breakdown
£3,412 total
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
30 Sept – 5 Oct
30 Sept – 5 Oct
£5,003 total
Show price breakdown
£5,003 total
4.99 out of 5 average rating, 70 reviews
4.99 (70)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in East Lyme
Walk to the beach at Black Point, Niantic, Ct
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
24–29 Oct
24–29 Oct
£813 total
Show price breakdown
£813 total
Free cancellation
4.98 out of 5 average rating, 171 reviews
4.98 (171)
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
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 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
£1,110
£991 total
Show price breakdown
5.0 out of 5 average rating, 64 reviews
5.0 (64)
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
11–16 Oct
11–16 Oct
£4,501 total
Show price breakdown
£4,501 total
4.96 out of 5 average rating, 23 reviews
4.96 (23)
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
27 Sept – 2 Oct
27 Sept – 2 Oct
£1,844
£1,693 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 East Hampton
Secluded Luxury: New Gunite Pool, Walk to Bay
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
20–25 Sept
20–25 Sept
£8,264
£5,363 total
Show price breakdown
5.0 out of 5 average rating, 58 reviews
5.0 (58)
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 29
Top guest favourite
Guest favourite
Home in East Hampton
Charming Home for a Perfect Escape
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
£4,405
£3,924 total
Show price breakdown
Free cancellation
4.93 out of 5 average rating, 15 reviews
4.93 (15)
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