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

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.

The Doctor’s 1781 House on the Litchfield Green

Welcome to the Doctor’s 1781 House on the Green in the Litchfield Historic District, a Registered Landmark. We are thrilled to share with our guests this beautifully preserved 1781 house and lush gardens in Connecticut’s quintessential colonial village. Located among historic homes and buildings and across the Green from Litchfield's charming restaurants and shops, walk in the footsteps of Washington, Tallmadge, Rochambeau, Harriet Beecher Stowe and other luminaries of America’s founding…

Peaceful Retreat 10 min from Mohawk Mtn w/ Sauna!

Modern riverside retreat on 14 private acres in Litchfield, 5 mins from Downtown. Spacious rooms, heated concrete floors, and a chef’s kitchen set the tone for relaxed luxury. With two primary suites, an infrared sauna, and river access after a few minutes walk through the forest, this home is perfect for families or friend getaways. You'll be minutes away from the best destinations in the area. Bantam Lake, Mohawk Mountain, and Litchfield’s delicious restaurants are a short drive away.

1800’s Farmhouse in the hills of Litchfield County

Welcome to our 1800s farmhouse on 2 acres in the hills of Litchfield County, surrounded by hiking trails, lakes, skiing, wineries, and the antique trail! This 4-bedroom home features a living room with wood-burning fireplace. Upstairs library/reading area with curated books. The dining room seats eight with pellet stove. Enjoy the outdoor dining area, grill, and fire pit. Very close to ski resorts, wineries, and lakes for kayaking/swimming, and many picturesque colonial towns!

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.

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

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!

Gray Rock Farm - The whole place to yourself

Gray Rock Farm has been in the family since 1949, and is still home to small flocks of sheep and chickens. Located four miles from the center of Litchfield, the location is ideally suited for a peaceful respite in the country. With enough room inside and out, this is the perfect place to get your whole family together. There is a level 2 EV charger. Please inquire about the charger before booking.

SerenityCT

New! Litchfield, Connecticut Nestled on 7 acres in the heart of a charming, quintessential New England town, our Chalet styled home offers a unique vacation rental. Enjoy the feel of nature without sacrificing the luxury of comfort. Experience rich history, nearby vineyards, hiking trails, breweries, nature and so much more!

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

Peaceful Barn Retreat

Newly Remodeled! *Upstairs* barn apartment stay 1 mile from Litchfield center. Situated halfway between South Farms and the center, across from the famed Arethusa Farm. You’ll be close enough to shops, restaurants, wineries and venues but in a tranquil setting all your own.