COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Southold Rentals

Updating...

age 0-16
315 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

315 Houses

Lakeside Cottage, Walk to Beach. Beautiful Sunsets

Southold cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$354

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

Southold house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$437

Southold Summer Home for rent

Southold house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$548

Beach Cottage, Bring The Dog, Founders Landing Beach, Southold, North Fork, NY

Southold house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$412

Price per night from

$674

Southold Contemporary Summer Home Steps from Beach and Vineyard

Southold house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$443

Private Waterfront W Beach, New Renovation

Southold house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$606

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

Southold house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$786

Shorecrest Beach House, 4 bedroom private beach front, new renovation

Southold house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$700

Great rentals within 20 miles that match your search

Beautiful-Pool,Tennis, Home Theater

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$406

Beautiful Guest House Waits For You - Hamptons - Sag Harbor

Sag Harbor guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$294

Modern Cottage top of house

Southampton house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$2,050

Family Sized Contemporary with Pool and Tennis

Sag Harbor house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,816

ROOM FOR YOU! MASTER SUITE IN HOUSE

Noyack b&b

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$393

7mins to beach, Bike/Walk to Sag Harbor Village

Sag Harbor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$879

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 33 minutes

Price per night from

$1,234

Historic Cottage Near Beach!

Greenport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$391

Hampton accommodations 2

East Hampton b&b

1 bedroom / 2 bathrooms / sleeps 2

Responds fast! avg. 45 minutes

Price per night from

$294

Hamptons Beach & Tennis Getaway

Amagansett house

1 bedroom / 3 bathrooms / sleeps 4

Price per night from

$352

Waterfront Community with pool and baybeach

Southampton house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$2,355

Summer Shangri La on Sag Harbor Memorial Day to Labor Day!!

Noyack house

5 bedrooms / 8 bathrooms / sleeps 10

Price per night from

$1,570

Luxury Hamptons Vacation Home w/NEW Pool, Tennis Court, Hot Tub

Quogue house

6 bedrooms / 5 bathrooms / sleeps 14

Responds fast! avg. 59 minutes

Price per night from

$1,060

Seahaven Resort Motel Unit 12

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$246

Relaxing East Hampton Summer Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$383

North Fork Loft - Perfect for Wine & Food Weekends

Mattituck apartment

5 bedrooms / 2 bathrooms / sleeps 14

Price per night from

$1,054

Seahaven Resort Motel Unit 1

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$235

Tropical Paradise -Year Round Indoor Pool

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$471

Renovated North Fork Home Close to Beach& Wineries

New Suffolk cottage

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$437

Seahaven Resort Motel Unit 10

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$270

Village traditional on a quiet cul de sac

Sag Harbor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,312

Charmimg Beach cottage in Sagaponack

Southampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$674

Estate In The Exclusive Georgica Pond Section Of East Hampton

East Hampton house

8 bedrooms / 8 bathrooms / sleeps 16

Responds fast! avg. 1 hour 33 minutes

Price per night from

$8,831

Sag Harbor Gathering House

Noyack house

5 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$2,944

Breathtaking Modern Lux Home in East Hampton - Private Garden & Pool Areas

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$1,767

Grace Cottage

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

“Welcome Respite” We've been lucky enough to stay at Grace Cottage a number of times and have always felt refreshed and grateful after our time there. Great sun rises, great sunsets only a short trip away. It's been relaxation at its best!

Price per night from

$589

Newly Remodeled Home Down the Street from the Beach & Short Drive to Vineyards

Sag Harbor chalet

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 31 minutes

Price per night from

$590

Rare Waterfront Experience :: Forever Bay Vistas ::

New Suffolk house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,139

Seahaven Resort Motel Unit 13

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$247

Viewing 38 of 315
rentals in Southold

×

Also consider