Top 50 Southold Vacation Rentals

Houses (2,206)
Cottages (272)
Estates (43)
Golf rental (1,590)
Beach view (461)
Beachfront (419)

Discover popular destinations in and around Southold

Osprey's Dominion

2,877 vacation rentals

Goldsmith's Inlet Park

2,830 vacation rentals

Horton Point Park

2,817 vacation rentals

Croteaux Vineyards

2,842 vacation rentals

Sparkling Pointe

2,820 vacation rentals

Mattebella Vineyards

2,846 vacation rentals

Corey Creek Winery

2,858 vacation rentals

The Old Field Vineyards

2,811 vacation rentals

Osprey's Dominion

2,877 vacation rentals

Goldsmith's Inlet Park

2,830 vacation rentals

Croteaux Vineyards

2,842 vacation rentals

Horton Point Park

2,817 vacation rentals

Sparkling Pointe

2,820 vacation rentals

Corey Creek Winery

2,858 vacation rentals

Mattebella Vineyards

2,846 vacation rentals

The Old Field Vineyards

2,811 vacation rentals

Explore a selection of Southold vacation rentals

Southold, NY- Heart of North Fork Wine Country
Guests10
Bedrooms4
Bathrooms3
Wonderful 4.5 / 5
$250 avg/night
4 beds
3 Bathrooms
Guests 10
2 reviews
Spacious Entertainer's Dream Home Close to Wineries/Beaches...
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$534 avg/night
4 beds
3 Bathrooms
Guests 10
36 reviews
Fabulous Waterfront Property in the Heart of Wine Country
Guests5
Bedrooms3
Bathroom1
Wonderful 4.9 / 5
$279 avg/night
3 beds
1 Bathroom
Guests 5
32 reviews
Beautifully appointed waterfront property with heated pool and...
Guests10
Bedrooms4
Bathrooms3
Wonderful 4.6 / 5
$634 avg/night
4 beds
3 Bathrooms
Guests 10
10 reviews
Lighthouse Inspired Lakefront Beach House, Overlooking Long Island...
Guests6
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$271 avg/night
4 beds
2 Bathrooms
Guests 6
6 reviews
Beautiful NEW Waterfront Paradise In Southold
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$621 avg/night
4 beds
3 Bathrooms
Guests 10
6 reviews
Beautifully Renovated Farmhouse with Gunite Saltwater Pool, 1/2...
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$637 avg/night
3 beds
2 Bathrooms
Guests 6
4 reviews
Perfect NoFork Location: Waterfront, Huge Yard, Kayaks and...
Guests7
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$303 avg/night
3 beds
2 Bathrooms
Guests 7
7 reviews
Renovated Home On Private Country Lane Close To Beaches...
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.9 / 5
$221 avg/night
4 beds
2 Bathrooms
Guests 10
11 reviews
Located in the heart of wine country/BEACHES/shops...
Guests8
Bedrooms3
Bathroom1
Wonderful 5 / 5
$375 avg/night
3 beds
1 Bathroom
Guests 8
14 reviews
Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub...
Guests10
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$446 avg/night
3 beds
2 Bathrooms
Guests 10
54 reviews
Perfect Family Vacation Home! Charming Waterfront Property close...
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$500 avg/night
3 beds
3 Bathrooms
Guests 8
11 reviews
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful...
Guests10
Bedrooms5
Bathrooms3
Wonderful 4 / 5
$929 avg/night
5 beds
3 Bathrooms
Guests 10
1 reviews
Great Location 2 Blocks from Private Beach!
Guests9
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$272 avg/night
4 beds
2 Bathrooms
Guests 9
2 reviews
Entertainers Delight Just Steps From The Beach
Guests14
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$338 avg/night
4 beds
3 Bathrooms
Guests 14
9 reviews
Beach Front in Southold; newly renovated/baths/kitchen/2nd floor...
Guests10
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$404 avg/night
4 beds
2 Bathrooms
Guests 10
8 reviews
Beachfront home on the North Fork
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$707 avg/night
3 beds
2 Bathrooms
Guests 8
3 reviews
2 Bedroom Apartment in Historic Home with private yard (WBH)
Guests4
Bedrooms2
Bathroom1
Wonderful 4.4 / 5
$214 avg/night
2 beds
1 Bathroom
Guests 4
23 reviews
Huge 6 Bedroom Home With Pool, Close To Beach and Wineries...
Guests14
Bedrooms6
Bathrooms4
Wonderful 4.7 / 5
$881 avg/night
6 beds
4 Bathrooms
Guests 14
3 reviews
North Fork Beach House
Guests7
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$327 avg/night
3 beds
2 Bathrooms
Guests 7
10 reviews
Southold Soundfront Private Beach
Guests4
Bedrooms2
Bathroom1
Wonderful 4.7 / 5
$485 avg/night
2 beds
1 Bathroom
Guests 4
9 reviews
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$1,500 avg/night
2 beds
1 Bathroom
Guests 4
7 reviews
Waterfront Colonial with Dock for boat or kayaks
Guests10
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$833 avg/night
5 beds
3 Bathrooms
Guests 10
13 reviews
Charming Waterfront Home with Private Dock Close to Vineyards...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$116 avg/night
3 beds
2 Bathrooms
Guests 8
21 reviews
Beautifully restored waterfront cottage in a spectacular setting!
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$282 avg/night
2 beds
1 Bathroom
Guests 4
37 reviews
Beach house in wine country; huge sun room, all new...
Guests5
Bedrooms2
Bathroom1
Wonderful 5 / 5
$338 avg/night
2 beds
1 Bathroom
Guests 5
7 reviews
Cute Cottage Apartment Near town, beaches and vineyards (WBH)
Guests4
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$228 avg/night
2 beds
1 Bathroom
Guests 4
17 reviews
North Fork Beach Retreat
Guests12
Bedrooms5
Bathrooms2
Wonderful 0 / 5
$500 avg/night
5 beds
2 Bathrooms
Guests 12
Family Friendly Getaway on the North Fork
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$292 avg/night
4 beds
3 Bathrooms
Guests 8
5 reviews
Renovated Cottage in Private North Fork Beach Community - LABOR...
Guests5
Bedrooms2
Bathroom1
Wonderful 5 / 5
$229 avg/night
2 beds
1 Bathroom
Guests 5
7 reviews
90 feet of private waterfront w beach, new renovation, panoramic...
Guests8
Bedrooms3
Bathrooms3
Wonderful 4.8 / 5
$433 avg/night
3 beds
3 Bathrooms
Guests 8
6 reviews
SOUTHOLD COTTAGE - Fully-Renovated One-Bedroom Cottage
Guests3
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$0 avg/night
1 bed
1 Bathroom
Guests 3
7 reviews
Southold. Immaculate 3 BR 2 bath ranch 180' to private beach
Guests6
Bedrooms3
Bathroom1
Wonderful 4.2 / 5
$214 avg/night
3 beds
1 Bathroom
Guests 6
5 reviews
Sweet Southold Beach Cottage Book now for 2018!
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$298 avg/night
2 beds
1 Bathroom
Guests 4
1 reviews
Beautiful North Fork 3-Bedroom Home 1000 Feet from a Private Sandy...
Guests4
Bedrooms3
Bathrooms3
Wonderful 4 / 5
$335 avg/night
3 beds
3 Bathrooms
Guests 4
1 reviews
Newly Renovated North Fork Beach & Wine Country Home
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.5 / 5
$375 avg/night
2 beds
2 Bathrooms
Guests 5
6 reviews
Beach Front, spacious 5 Bedrooms, North Fork, Long Island
Guests12
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$484 avg/night
5 beds
3 Bathrooms
Guests 12
4 reviews
Sprawling North Fork Retreat
Guests12
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$443 avg/night
4 beds
2 Bathrooms
Guests 12
2 reviews
North Fork Easy Breezy Coastal Comfort
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$325 avg/night
3 beds
2 Bathrooms
Guests 6
1 reviews
Lakefront Beach Home/Walk to Kenney's Beach
Guests6
Bedrooms3
Bathroom1
Wonderful 5 / 5
$290 avg/night
3 beds
1 Bathroom
Guests 6
2 reviews
Perfect family summer getaway
Guests10
Bedrooms5
Bathrooms2
Wonderful 0 / 5
$350 avg/night
5 beds
2 Bathrooms
Guests 10
Private Waterfront Compound
Guests10
Bedrooms3
Bathroom1
Wonderful 0 / 5
$343 avg/night
3 beds
1 Bathroom
Guests 10
Curated Country Living In A Historic Farmhouse
Guests7
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$789 avg/night
3 beds
2 Bathrooms
Guests 7
6 reviews
Charming Southold Cottage near beaches and vineyards
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$304 avg/night
2 beds
2 Bathrooms
Guests 6
11 reviews
Southold home at Kenney's Beach 4 bedrooms
Guests8
Bedrooms4
Bathrooms2
Wonderful 4 / 5
$385 avg/night
4 beds
2 Bathrooms
Guests 8
1 reviews
Newly Remodeled Summer Escape W/ Pool & Access To Beach
Guests12
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$171 avg/night
4 beds
4 Bathrooms
Guests 12
CHARMING COTTAGE ON LONG ISLAND SOUND, PRIVATE BEACH, GLORIOUS...
Guests6
Bedrooms2
Bathroom1
Wonderful 5 / 5
$350 avg/night
2 beds
1 Bathroom
Guests 6
7 reviews
Walk to the beach and Southold town! Outdoor bar, brand new chef's...
Guests11
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$550 avg/night
4 beds
2 Bathrooms
Guests 11
15 reviews
Private Waterfront Compound
Guests10
Bedrooms5
Bathroom1
Wonderful 0 / 5
$500 avg/night
5 beds
1 Bathroom
Guests 10
Breathtaking Waterfront Views - In The Middle of Wine Country...
Guests8
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$599 avg/night
4 beds
2 Bathrooms
Guests 8
25 reviews

Southold, NY, USA Vacation Rentals

Discover popular destinations in and around Southold

Southold, NY- Heart of North Fork Wine Country

Spacious Entertainer's Dream Home Close to Wineries/Beaches...

Fabulous Waterfront Property in the Heart of Wine Country

Beautifully appointed waterfront property with heated pool and...

Lighthouse Inspired Lakefront Beach House, Overlooking Long Island...

Beautiful NEW Waterfront Paradise In Southold

Beautifully Renovated Farmhouse with Gunite Saltwater Pool, 1/2...

Perfect NoFork Location: Waterfront, Huge Yard, Kayaks and...

Renovated Home On Private Country Lane Close To Beaches...

Located in the heart of wine country/BEACHES/shops...

Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub...

Perfect Family Vacation Home! Charming Waterfront Property close...

5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful...

Great Location 2 Blocks from Private Beach!

Entertainers Delight Just Steps From The Beach

Beach Front in Southold; newly renovated/baths/kitchen/2nd floor...

Beachfront home on the North Fork

2 Bedroom Apartment in Historic Home with private yard (WBH)

Huge 6 Bedroom Home With Pool, Close To Beach and Wineries...

North Fork Beach House

Southold Soundfront Private Beach

One Of A Kind, Resort- Like Waterfront Cottage In Wine Country

Waterfront Colonial with Dock for boat or kayaks

Charming Waterfront Home with Private Dock Close to Vineyards...

Beautifully restored waterfront cottage in a spectacular setting!

Beach house in wine country; huge sun room, all new...

Cute Cottage Apartment Near town, beaches and vineyards (WBH)

North Fork Beach Retreat

Family Friendly Getaway on the North Fork

Renovated Cottage in Private North Fork Beach Community - LABOR...

90 feet of private waterfront w beach, new renovation, panoramic...

SOUTHOLD COTTAGE - Fully-Renovated One-Bedroom Cottage

Southold. Immaculate 3 BR 2 bath ranch 180' to private beach

Sweet Southold Beach Cottage Book now for 2018!

Beautiful North Fork 3-Bedroom Home 1000 Feet from a Private Sandy...

Newly Renovated North Fork Beach & Wine Country Home

Beach Front, spacious 5 Bedrooms, North Fork, Long Island

Sprawling North Fork Retreat

North Fork Easy Breezy Coastal Comfort

Lakefront Beach Home/Walk to Kenney's Beach

Perfect family summer getaway

Private Waterfront Compound

Curated Country Living In A Historic Farmhouse

Charming Southold Cottage near beaches and vineyards

Southold home at Kenney's Beach 4 bedrooms

Newly Remodeled Summer Escape W/ Pool & Access To Beach

CHARMING COTTAGE ON LONG ISLAND SOUND, PRIVATE BEACH, GLORIOUS...

Walk to the beach and Southold town! Outdoor bar, brand new chef's...

Private Waterfront Compound

Breathtaking Waterfront Views - In The Middle of Wine Country...