Holiday houses in Litchfield

The oldest home in Litchfield.

You will simply fall in love with The Red House 1735! Cozy antique home adorned with vintage treasures. Conveniently located near everything the area has to offer. Walk across the street to White Memorial Conservation, with some of the most beautiful trails in Litchfield County. 5 minute drive to the town of Litchfield with quaint shops and restaurants. Bantam Lake, CT Wine Trails, Mohawk Ski Mountain, and so much more is within a short driving distance. We welcome you to enjoy our country oasis

Location · Family · Outdoor spaces

The Cottage @ 228 Maple

This charming, fully equipped 2-story home is privately set at the edge of the woods. Five minute drive to the historic Litchfield Center, this gem is central to everything, making it easy to plan your visit. History walks, museums, restaurants, boutiques, antiques, wineries, distilleries, & farmers markets. Yearlong recreational activities -hiking, biking, birding, boating, skiing nearby at Bantam Lake, White Memorial, Mohawk Ski Area, Topsmead State Forest, Land Trust & Audubon Preserves.

Location · Family · Accuracy

Fully Renovated Rural Barn

Newly renovated barn on a quiet rural road yet close to all the attractions of Southern Litchfield County. The light-filled barn has two large patio doors into a substantial living and entertaining area with a large sectional sofa-bed, a dining table for 10 and adjacent kitchen area with an island. There is a downstairs washroom. A large light-filled upstairs sleeping area has a king-size bed and a bathroom with shower. Outside is a patio dining area and parking in a dedicated driveway.

Family · Value · Sleep quality

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Location · Family · Bathroom

Country Suite

Situated above a charming residential barn this cozy two room suite offers comfort and privacy for those traveling through bucolic Litchfield CT This airy loft boasts Fiberoptic WiFi Smart TV automatic outside lighting A large bedroom overlooks the front of the property in this quiet wooded neighborhood large enough to have a king size bed large bathroom work space and kitchenette Keurig and coffee incl. The front room faces a sweeping lawn on this well kept property

Location · Family · TV

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Family · Location · Checkout

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Location · Value · Long stay

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area

Value · Location · Heating

The Litchfield Nook - Cozy Uptown Apartment

Welcome to a cozy and peaceful nook in the hills! This well appointed apartment provides a home away from home feel. The unit is located on the first floor of a multi unit family house and sleeps 4 comfortably. You will be within walking distance to the iconic Litchfield Green and White Memorial Foundation. Everything that there is to see and do in Litchfield is within a short driving distance. Enjoy the beauty of Litchfield and come join us as our guest!

Value · Family · Condition

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Value · Family · Sleep quality

Hemlock Hill Suite

Escape to the charm of Litchfield, Connecticut, and unwind in this beautifully designed guest suite where modern luxury meets classic New England character. Attached to an 1820 colonial home and centrally located to all that the area has to offer, the suite features a king size Tuft & Needle bed, bespoke deVol kitchen with Smeg appliances, Parachute linens, and a Samsung Frame TV. The loft is not accessible to guests.

Location · Family · Comfort

Beautiful Brook-side Log Cabin on 3 Private Acres

Fall asleep to the sound of the rushing brook in this beautifully restored log home. The cabin sits in the middle of three wooded acres overlooking Catlin Brook as it cascades through the gorge below. It seems like wilderness, yet all the amenities of Harwinton are just a few minutes away.

Location · Value · Checkout