Southold Vacation Rentals

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Vacation Rentals in Southold

Hamptons Contemporary 4 beds cozy home minutes to beaches, village, US Open disc

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 Shinnecock Hills Golf Course and The Hamptons Beaches.

Washer

Dryer

Near the Hamptons - Private Pool, Jacuzzi Retreat

Calverton NY

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

Pool

Hot Tub

Modern Quogue Escape with Pool & Pool House, Luxurious Indoor-Outdoor...

East Quogue NY

With a stay at this vacation home in East Quogue, you'll be near the beach, within a 15-minute drive of Shinnecock Hills Golf Course and Regal UA Hampton Bays.

Pool

Kitchen

Cozy 3-Bedroom Cape House Near Havens Beach

Sag Harbor NY

When you stay at this vacation home in Sag Harbor, you'll be on the beach, within a 5-minute walk of The Hamptons Beaches and Havens Beach.

Kitchen

Washer

Cozy 5 Bedroom With Wi-fi And Air Condition

Wainscott NY

$1,707 nightly

$1,950 total

Jun 10 - Jun 11

Total with taxes and fees

With a stay at this vacation home in Wainscott, you'll be within a 10-minute drive of The Hamptons Beaches and SagPond Vineyards.

Air conditioning

Charming Waterfront Getaway — South Cove, Old Saybrook

Old Saybrook CT

Located in Old Saybrook, this vacation home is within a 5-minute drive of General William Hart House and Katharine Hepburn Cultural Arts Center.

Washer

Dryer

Waterfront Lakehouse w/Hot Tub in Clinton, CT. Pet-Friendly!

Clinton CT

With a stay at this vacation home in Clinton, you'll be within a 10-minute drive of Hammonasset Beach State Park and Clinton Crossing Premium Outlets.

Hot Tub

Kitchen

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

Southampton NY

$743 nightly

$849 total

Jun 12 - Jun 13

Total with taxes and fees

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

The SandPiper

Greenport, NY

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

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

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

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

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12

Guilford CT

With a stay at this vacation home, you'll be centrally located in Guilford, within a 15-minute drive of Hammonasset Beach State Park and Guilford Town Green.

Pool

Kitchen

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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.