Southold Vacation Rentals

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Vacation Rentals in Southold

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton NY

Located in Southampton, this vacation home is within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.

Pool

Hot Tub

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

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Hampton Bays NY

When you stay at this vacation home in Hampton Bays, you'll be on the waterfront, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.

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 Cooper's Beach.

Pool

Kitchen

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

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.

Hot Tub

Kitchen

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

Cozy beach hose minutes from Hamptons

Calverton NY

$630 nightly

$719 total

Apr 24 - Apr 25

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

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

Enjoy the perfect summer escape in this beautiful home in the Hamptons.

East Hampton NY

With a stay at this vacation home in East Hampton (East Hampton North), you'll be within a 5-minute drive of The Hamptons Beaches and Amelia Cottage Museum.

Pool

Kitchen

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

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

Kitchen

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead NY

With a stay at this vacation home in Riverhead, you'll be within a 15-minute drive of Splish Splash Water Park and Roanoke Vineyards.

Hot Tub

Kitchen

Direct Waterfront Beach House with Panoramic Views

East Lyme CT

When you stay at this vacation home in Niantic, you'll be on the beach, within a 10-minute walk of Attawan Beach and McCook Point Beach.

Kitchen

Washer

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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.