Holiday rentals in Litchfield County

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

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.

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

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!

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 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.

Litchfield Luxury Home w/Heated Pool

Escape to this fully renovated 4BR, 2.5BA estate on 12 private acres with sweeping views of Litchfield’s hills. Enjoy a heated pool (seasonal @ $50 per day upcharge), private gym, and walking trails. Inside, relax in beautifully furnished spaces with hardwood floors and New England charm. Just 3 miles from downtown Litchfield’s shops, dining, and hiking. Whether you’re sipping coffee while watching the sunrise or relaxing at sunset by the pool, the views are breathtaking year-round.

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 Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

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.

County Seat Colonial/Walk to Town-HOST&Co

Welcome to your home away from home. Nestled in the charming Historic District of Litchfield, this inviting getaway puts you just steps from fine dining, boutique shopping, delightful bakeries, and iconic landmarks. Whether you’re exploring the town or staying in, you’ll find everything you need—from spacious, comfortable living areas to a fully equipped kitchen perfect for preparing fresh, local fare from the nearby farmers market.