Southold Cottages

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

Cottages in Southold

North Fork Resort

690 Queen St Greenport NY

$409 nightly

$467 total

Jul 19 - Jul 20

Total with taxes and fees

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

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT

$234 nightly

$265 total

Jul 23 - Jul 24

Total with taxes and fees

With a stay at this cottage in Clinton, you'll be within a 10-minute drive of Hammonasset Beach State Park and Clinton Plaza Shopping Center.

'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.

Fairy Tale Guest Cottage in Magic Garden by Pool

Bridgehampton NY

When you stay at this cottage in Bridgehampton, you'll be by the sea, a 3-minute drive from Wolffer Estates Vineyard and 7 minutes from The Hamptons Beaches.

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.

2 mins/350 ft walk to West Beach, relaxing 3-BR sleeps 8 cottage with large yard

Westbrook CT

With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 15-minute drive of Hammonasset Beach State Park and Westbrook Town Beach.

Seabreeze 4 Charming Cottage footsteps to beach

Hampton Bays NY

$548 nightly

$588 total

Jul 19 - Jul 20

Total with taxes and fees

When you stay at this cottage in Hampton Bays, you'll be near the beach, a 1-minute drive from The Hamptons Beaches and 6 minutes from Shinnecock Hills Golf Course.

Ritz - East Hampton Cottage On The Water

East Hampton NY

When you stay at this cottage in East Hampton, you'll be next to a golf course, within a 15-minute walk of The Hamptons Beaches and Three Mile Harbor.

The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton CT

With a stay at this cottage in Clinton, you'll be within a 10-minute drive of Hammonasset Beach State Park and Adam Stanton House and General Store Museum.

2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

Westbrook CT

With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 15-minute drive of Hammonasset Beach State Park and Westbrook Town Beach.

Hamptons Waterfront- Great Location!

Hampton Bays NY

When you stay at this cottage in Hampton Bays, you'll be on the beach, a 3-minute drive from The Hamptons Beaches and 6 minutes from Shinnecock Hills Golf Course.

Walk to Breakwater Beach in Heart of Wine Country

Mattituck NY

Located in Mattituck, this cottage is on the waterfront, within a 10-minute drive of Love Lane and Macari Vineyards.

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.