Holiday houses in Litchfield County

Luxury Rural Barn

Renovated luxury 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 is in the dedicated driveway.

Family · Value · Pets

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

Family · Location · Nearby

Halo Hollow Haus - Litchfield Lake & Ski Haven

Rest, relax, and recharge in this serene and stylish space. Halo Hollow Haus is a lake house and ski lodge offering boutique vacation vibes and year-round country beauty. Nestled in the beautiful Woodridge Lake community, you'll enjoy lake life at its finest while just minutes away from all that Litchfield County has to offer. Enjoy classic New England towns, swimming, skiing, hiking, fishing, parks, golf, mountains, foliage, antiquing, vineyards, excellent restaurants, and cultural attractions.

Family · Location · Checkout

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

Value · Location · Wi-Fi

Cozy Cabin, Fall Foliage, Lake

Escape daily stress at Deer Ridge Cabin CT, a bright and airy retreat with all amenities. Enjoy the private community beach and paddleboarding at the lake, a 5-minute walk away. Or exploring nearby hiking trails. Only a 15-min drive to downtown Lichfield to indulge in great restaurants and shopping. Experience local wineries. Conveniently located 2 hrs from NYC, this peaceful cabin offers a quick escape to nature while being close to everything! Deer Ridge Cabin CT is your perfect getaway!

Location · Value · Layout

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 · Value · Hiking

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.

Family · Value · Access

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 · Value · Kitchen

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 · Family · View

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!

Family · Value · Amenities

Litchfield County Farmhouse with a Modern Twist

Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Family · Location · Long stay

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!

Family · Location · Comfort