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Search results; Over 1,000 homes in Southold
Over 1,000 homes in Southold
Photo 1 of 6
Top guest favourite
Guest favourite
Guest suite in Southold
Comfortable Suite, a walk to the beach
1 bedroom
,
·
1 bed
,
·
1 private bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
£1,132
total
Show price breakdown
£1,132 total
,
·
4.94 out of 5 average rating, 156 reviews
4.94 (156)
Photo 1 of 6
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 Sept
1–8 Sept
£12,538
total
Show price breakdown
£12,538 total
Free cancellation
4.94 out of 5 average rating, 35 reviews
4.94 (35)
Photo 1 of 6
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
20–25 Sept
20–25 Sept
£4,426
total
Show price breakdown
£4,426 total
4.95 out of 5 average rating, 22 reviews
4.95 (22)
Photo 1 of 6
Home in Cutchogue
Steps to Beach, Vineyards, Farm Stands & Village
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
£3,362
total
Show price breakdown
£3,362 total
New place to stay
New
Photo 1 of 6
Home in Greenport
Greenport Beachfront Home | Private Beach & Sunset
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
£4,257
total
Show price breakdown
£4,257 total
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 6
Home in Sag Harbor
Striking Waterfront 3 Bedroom on Sag Harbor Cove
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
20–25 Sept
20–25 Sept
£4,217
£2,241
total
Show price breakdown
New place to stay
New
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Southold
Luxury by the Sea!!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
7–12 Sept
7–12 Sept
£4,022
total
Show price breakdown
£4,022 total
4.95 out of 5 average rating, 56 reviews
4.95 (56)
Photo 1 of 6
Home in Water Mill
Secluded Oasis | 3 Acres, Heated Pool & Fire Pit
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
1–6 Sept
1–6 Sept
£6,765
total
Show price breakdown
£6,765 total
Free cancellation
New place to stay
New
Photo 1 of 6
Top guest favourite
Guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms
2 bedrooms
,
·
3 queen beds
3 queen beds
,
·
No bathroom
No bathroom
20–25 Sept
20–25 Sept
£1,429
total
Show price breakdown
£1,429 total
Free cancellation
5.0 out of 5 average rating, 99 reviews
5.0 (99)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Cutchogue
Sunny Harbor Suite
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
26–31 Oct
26–31 Oct
£747
total
Show price breakdown
£747 total
Free cancellation
4.96 out of 5 average rating, 25 reviews
4.96 (25)
Photo 1 of 6
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
7–14 Sept
7–14 Sept
£4,032
£3,725
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 6
Top guest favourite
Guest favourite
Place to stay in Cutchogue
Sunset Suite - walk to vineyards, beaches, & more
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
£910
£795
total
Show price breakdown
Free cancellation
4.98 out of 5 average rating, 201 reviews
4.98 (201)
Photo 1 of 6
Superhost
Superhost
Home in East Hampton
East Hampton Rental w/ Pool, Moments to Amenities
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
11–16 Oct
11–16 Oct
£2,668
£2,389
total
Show price breakdown
5.0 out of 5 average rating, 92 reviews
5.0 (92)
Photo 1 of 6
Room in Southold
The Terry Inn Master Suite
1 bed
1 bed
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
£2,215
total
Show price breakdown
£2,215 total
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Shelter Island
Shelter island retreat
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
£2,192
total
Show price breakdown
£2,192 total
Free cancellation
4.97 out of 5 average rating, 172 reviews
4.97 (172)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in East Marion
Bohemian Old Life Saving Station with Beach & Pool
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
4 bathrooms
4 bathrooms
8–15 Sept
8–15 Sept
£10,650
total
Show price breakdown
£10,650 total
4.97 out of 5 average rating, 114 reviews
4.97 (114)
Photo 1 of 6
Home in Southold
Waterfront, Dock, Boat Ramp, Hot Tub & Beaches
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
7–12 Sept
7–12 Sept
£5,273
total
Show price breakdown
£5,273 total
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Southold
Peconic Pearl Cottage
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
£3,147
£2,786
total
Show price breakdown
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Photo 1 of 6
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3.5 bathrooms
3.5 bathrooms
13–18 Sept
13–18 Sept
£5,588
total
Show price breakdown
£5,588 total
Free cancellation
New place to stay
New
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