Vacation 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.

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

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.

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.

Cozy Cottage |Quintessential CT | Pet Friendly

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

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.

Chic Colonial Charmer near Litchfield Green

Welcome to Sedgewick House! This beautifully restored 1825 colonial marries vintage charm with modern amenities. Filled with funky designer interiors, a fully equipped kitchen, large private backyard and cozy spaces doused in natural light, this retreat offers character and comfort in equal measure. Ideal for those wanting to experience the quaint town of Litchfield with a boutique stay. Walk to some of our favorite restaurants or grill from the comfort of your patio.

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!

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.