Litchfield 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

Cottages in Litchfield

The Blue Elm - A Historic Berkshire Cottage

Sheffield MA

Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.

Kitchen

Free WiFi

Idillic summer getaway in Litchfield Hills, CT.

Sharon CT

When you stay at this cottage in Sharon, you'll be on a river, within a 5-minute drive of Housatonic Meadows State Park and West Cornwall Covered Bridge.

The Cottage at Highland Lake, year-round, waterfront with a boat dock

Winsted CT

With a stay at this cottage in Winchester, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 9 minutes by foot from The Marina at Highland Lake.

Cozy 2-bedroom Cottage with Access to Bantam Lake

Morris CT

With a stay at this cottage in Morris, you'll be on a lake, just steps from Bantam Lake and a 2-minute drive from Camp Columbia State Park.

Kitchen

Washer

Ashley Falls Home w/ Fire Pit: Hike & Ski!

Ashley Falls MA

Located in Ashley Falls, this cottage is within a 5-minute drive of Ashley Falls Woods and Bartholomew's Cobble.

Kitchen

Parking included

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown CT

Located in Watertown, this cottage is on a lake, within a 15-minute drive of Glebe House Museum and The Gertrude Jekyll Garden and Bariatric Summit.

Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville CT

Located in Lakeville, this cottage is on a lake, a 4-minute drive from Holley-Williams House Museum and 6 minutes from North East Town Hall.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Plymouth CT

Located in Plymouth, this cottage is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.

Kitchen

Washer

Pool & Private Acreage: Luxe Hudson Valley Home

Pine Plains NY

When you stay at this cottage in Pine Plains, you'll be within a 10-minute drive of The Stissing Center and Pine Plains Library.

Charming Connecticut Retreat Near Museums & Hiking

Waterbury CT

Located in Waterbury, this cottage is within a 5-minute drive of Carrie Welton Fountain and Palace Theatre.

Lakefront Home, Close to Mt Southington!

1743 Meriden Rd Wolcott CT

With a stay at this cottage in Wolcott, you'll be within a 5-minute drive of Mattatuck Beach and Mount Southington Ski Area.

Squantz Pond Oasis, charming cottage, Firepit and lake view

New Fairfield CT

With a stay at this cottage in New Fairfield, you'll be within a 10-minute drive of Candlewood Lake and Squantz Pond State Park.

Don't see what you're looking for?

See all available properties in Litchfield

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.