Southold Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Southold hotels

Vacation Rentals in Southold

Exquisite New Hampton Home in a Perfect Location

East Hampton NY

With a stay at this vacation home in East Hampton, you'll be by the ocean, within a 10-minute drive of The Hamptons Beaches and Three Mile Harbor.

Pool

Kitchen

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Southampton NY

With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Shinnecock Hills Golf Course.

Pool

Kitchen

!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !

Wainscott NY

With a stay at this vacation home in Wainscott, you'll be next to a golf course, within a 5-minute drive of The Hamptons Beaches and The Clubhouse Hamptons.

Pool

Hot Tub

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Southold NY

Located in Southold, this vacation home is on the waterfront, within a 5-minute drive of Croteaux Vineyards and Mattebella Vineyards.

Kitchen

Washer

Storybook Cottage

Old Saybrook CT

With a stay at this vacation home in Old Saybrook, you'll be within a 5-minute drive of Essex Saybrook Antique Village Shopping Center and Yale New Haven Health Old Saybrook Medical Center.

Kitchen

Washer

Seashell – Short Walk to Long Beach, Heated Pool & Best Sunsets in the Hamptons

Sag Harbor NY

When you stay at this vacation home in Sag Harbor, you'll be by the sea, within a 15-minute walk of The Hamptons Beaches and Foster Memorial Town Beach.

Pool

Kitchen

Cozy beach hose minutes from Hamptons

Calverton NY

$763 nightly

$871 total

Jul 27 - Jul 28

Total with taxes and fees

With a stay at this vacation home in Calverton, you'll be within a 10-minute drive of Splish Splash Water Park and Wildwood State Park.

Kitchen

Washer

Gorgeous Historical 6 bdrm House close to vineyards and breweries,

Peconic NY

Located in Peconic, this vacation home is in a rural location, within a 5-minute drive of Sannino's Bella Vita Vineyard and Raphael Winery.

Kitchen

Free WiFi

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach

Westhampton Beach NY

With a stay at this vacation home in Westhampton Beach, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and The Great Lawn.

Pool

Hot Tub

Completely Renovated Modern Hampton Bays Retreat with Brand New Pool,...

Hampton Bays NY

When you stay at this vacation home in Hampton Bays, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Shinnecock Hills Golf Course.

Pool

Kitchen

Aqua Vista

Greenport, NY

$566 nightly

$647 total

Aug 12 - Aug 13

Total with taxes and fees

With a stay at this vacation home in Greenport (Pipes Cove), you'll be steps from Railroad Museum of Long Island and 3 minutes by foot from East End Seaport Maritime Museum.

Kitchen

Washer

Peaceful and Private 4-Bedroom Home in Southampton

Southampton NY

With a stay at this vacation home in Southampton, you'll be within a 15-minute drive of The Hamptons Beaches and Shinnecock Hills Golf Course.

Hot Tub

Kitchen

Don't see what you're looking for?

See all available properties in Southold

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.