1,321 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Barns
Bungalows
Cabins
Chalets
Condos
Cottages
Estates
Farmhouses
Hotels
Homes
Lodges
Studios
Townhomes
Villas
Yachts
Boats
Castles

Booking Options

Location Type

Even More Filters

Features

Managed By

1,321 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Southold: Houses, Cottages & More | Page 2(1,321)

1,321 Results
$600 - $1,000
per night
3 - 31 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 31 night min stay
(14)
$485
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night min stay
(6)
  • 8 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 16
3 - 6 night min stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 8
4 - 14 night min stay
2 Reviews
$5,000 - $7,500
per week
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 6
7 - 14 night min stay
1 Review
$7,500 - $25,667
per week
7 - 30 night min stay
  • 5 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 10
7 - 30 night min stay
(18)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 night min stay
1 Review
  • 5 BR,
  • 3 BA,
  • Sleeps 9
7 night min stay
(15)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
$4,500 - $7,000
per week
7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 5
7 night min stay
1 Review
$3,000 - $4,500
per week
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
7 - 14 night min stay
$600 - $1,750
per night
3 - 7 night min stay
  • 6 BR,
  • 7 BA,
  • Sleeps 15
3 - 7 night min stay
2 Reviews
$833 - $1,250
per night
6 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
6 - 30 night min stay
2 Reviews
$1,300
per night
2 - 6 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 8
2 - 6 night min stay
2 Reviews
$600 - $750
per night
3 - 4 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 - 4 night min stay
2 Reviews
$850 - $1,200
per night
1 - 3 night min stay
  • 6 BR,
  • 3 BA,
  • Sleeps 10
1 - 3 night min stay
(5)
$3,000 - $4,200
per week
7 - 30 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
7 - 30 night min stay
2 Reviews
$857 - $1,267
per night
1 - 30 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
1 - 30 night min stay
2 Reviews
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 night min stay
(4)
$1,429 - $2,857
per night
2 - 7 night min stay
  • 6 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 16
2 - 7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
14 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
1 - 7 night min stay
2 Reviews
  • 7 BR,
  • 5 BA,
  • Sleeps 13
1 - 7 night min stay
(5)
$1,800 - $2,625
per night
6 night min stay
  • 5 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
6 night min stay
1 Review
$5,000 - $8,000
per week
14 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
14 night min stay
  • 5 BR,
  • 5 BA,
  • Sleeps 10
14 night min stay
$1,500 - $2,000
per night
3 night min stay
  • 5 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
3 night min stay
  • 5 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
2 Reviews
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night min stay
 View map Map
Advertisement