Southold Vacation Rentals

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Vacation Rentals in Southold

Beautiful Hamptons home close to beaches, shopping, & restaurants!

Hampton Bays NY

With a stay at this vacation home in Hampton Bays, you'll be within a 5-minute drive of The Hamptons Beaches and Good Ground Park.

Pool

Kitchen

New Madison beach house - Ocean front- Great views- booking Summer 2026

Madison CT

Located in Madison, this vacation home is by the ocean, within a 10-minute drive of Madison Green Historic District and Deacon John Grave House.

Kitchen

Washer

Beach House

East Lyme CT

Located in Niantic, this vacation home is by the sea, a 3-minute drive from Attawan Beach and 6 minutes from McCook Point Beach.

Hot Tub

Kitchen

Beach, Pool, Wine, Shopping!

Mattituck NY

Located in Mattituck, this vacation home is in a rural location, a 2-minute drive from Love Lane and 6 minutes from Pellegrini Vineyards.

Pool

Kitchen

Welcome to your serene escape in East Hampton! 3-bedroom, 2.5 bathrooms with AC

East Hampton NY

With a stay at this vacation home in East Hampton, you'll be within a 15-minute walk of The Hamptons Beaches and Three Mile Harbor.

Pool

Washer

Hamptons Retreat 1/4 Mi to Viral Supermodel Cafe to Bethenny Frankel's Pop-Up!

east quogue NY

With a stay at this vacation home in East Quogue, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Quogue Community Hall.

Kitchen

Washer

TREETOPS house! AUG openings! A Reunion/Retreat estate! Seasonal POOL! Sleeps 12

Guilford CT

A stay at this vacation home places you in the heart of Guilford, within a 5-minute drive of Guilford Town Green and Hyland House Museum.

Pool

Kitchen

Cozy beach hose minutes from Hamptons

Calverton NY

$732 nightly

$836 total

Sep 9 - Sep 10

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

The SandPiper

Greenport, NY

$316 nightly

$360 total

Sep 10 - Sep 11

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

Cozy Hampton Bays Retreat — Just 9 Minutes to Ponquogue Beach

Hampton Bays NY

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

Kitchen

Washer

Luxurious midcentury modern glass house in the woods, chefs kitchen & great art

Old Lyme CT

Located in Old Lyme, this vacation home is on a lake, within a 5-minute drive of Goose Island and Lawrence & Memorial Family Medicine.

Kitchen

Washer

Phenomenal One Bedroom Cottage in Historic Old Lyme, Connecticut

Old Lyme CT

With a stay at this vacation home in Old Lyme, you'll be within a 15-minute walk of Old Lyme Historical Society and Connecticut River.

Kitchen

Air conditioning

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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.