Southold Cottages

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Cottages in Southold

North Fork Cottages & RV Resort

690 Queen St Greenport NY

Located in Greenport, North Fork Cottages & RV Resort is within a 5-minute drive of Kontokosta Winery and Stony Brook Eastern Long Island Hospital.

Pool

Pet friendly

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

greenport NY

Located in Greenport (Pipes Cove), this cottage is within a 15-minute walk of Railroad Museum of Long Island and East End Seaport Maritime Museum.

RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.

Westbrook CT

With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Chalker Beach and Westbrook Town Beach.

Direct waterfront renovated cottage.

Madison CT

With a stay at this cottage in Madison (Madison Center), you'll be within a 5-minute drive of Deacon John Grave House and Anna Mia's.

Seabreeze #3: Cozy Cottage by the beach

Hampton Bays NY

$400 nightly

$457 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this cottage in Hampton Bays, you'll be steps from The Hamptons Beaches and a 2-minute drive from Meschutt Beach.

Kitchen

Pet friendly

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue NY

When you stay at this cottage in Cutchogue, you'll be near the beach, within a 5-minute drive of Bedell Cellars and Pindar Vineyards.

Lovely Cottage in the Heart of Long Island Wine country

Southold NY

When you stay at this cottage in Southold, you'll be on the waterfront, within a 5-minute drive of Horton Lane Beach and Sparkling Pointe.

Adorable Cottage with Cottage porch, walk to water & town

Westbrook CT

With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.

Charming 3-bedroom cottage short walk to Chalker Beach

Old Saybrook CT

With a stay at this cottage in Old Saybrook (Saybrook Manor), you'll be within a 5-minute drive of Chalker Beach and Saybrook Country Barn.

Luxury Tiny Home In Niantic

East Lyme CT

With a stay at this cottage in Niantic, you'll be within a 5-minute drive of Rocky Neck State Park and The Book Barn.

Hamptons Vacation Rental w/ Seasonal Pool!

Hampton Bays NY

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

The Little Red Cottage - A cozy home steps away from private beach & wine trail.

Baiting Hollow NY

When you stay at this cottage in Riverhead, you'll be by the sea, within a 5-minute drive of Roanoke Vineyards and Baiting Hollow Hummingbird Sanctuary.

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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.