Vacation rentals in Litchfield County

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Top-rated vacation rentals in Litchfield County

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Top guest favorite

The exterior of the rental space features light-colored siding with a welcoming black door. A small outdoor dining area is provided with a round table and chairs, nestled beside a well-maintained garden area with greenery and stone accents.

Guest suite in Bethlehem

4.99 out of 5 average rating, 311 reviews

Quiet cottage w/chickens, gardens near Litchfield

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and summer fun!

Superhost

A two-story blue house is framed by lush green trees and shrubs, creating a natural setting. A bright red door serves as an inviting focal point, while a stone path leads to the entrance, enhancing accessibility.

Home in Litchfield

4.83 out of 5 average rating, 389 reviews

Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ

Enjoy the comfort of home with air conditioning, heating, dedicated workspace, TV, and Wi-Fi. Cook your meals in the fully-stocked kitchen with all the essentials. Pamper yourself in the private bathtub or shower with provided body soap, shampoo and conditioner. Relax in the hot tub or lounge in the backyard with an outdoor dining area, bbq, patio, and fire pit. 3 Min - Litchfield Town 4 Min - Arethusa Dairy farm 5 Min - White Memorial Conservation Center 16 Min - Mohawk Mountain Ski Area

Guest favorite

A well-maintained garden is framed by a wooden fence, featuring vibrant sunflowers and lush greenery. The manicured lawn surrounds the garden, creating a serene outdoor space. Towering trees provide a natural backdrop, enhancing the peaceful ambiance of the area.

Guest suite in Litchfield

4.95 out of 5 average rating, 116 reviews

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 WiFi cable TV a hi-tech key free security lock 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

Top guest favorite

A cozy living room features a comfortable gray sofa adorned with colorful cushions, accompanied by a wooden coffee table. Two chairs, one with burgundy upholstery and the other with a light wood finish, add seating options. Soft lighting is provided by two table lamps and recessed lights.

Apartment in Litchfield

4.99 out of 5 average rating, 140 reviews

Litchfield Hills Hideaway

Enjoy the Litchfield Hills from this newly renovated one bedroom apartment with private entrance. Amenities include full kitchen, living room, bedroom with queen bed, and full en suite bathroom. WiFi and cable TV included. All located less than 2 miles from historic Litchfield Center. Our property borders on the White Memorial Foundation nature preserve, with over 40 miles of hiking trails. Mohawk Mountain Ski area in Cornwall and Ski Sundown in New Hartford are only a short drive away.

Guest favorite

A modern black cottage is presented, set against a backdrop of tall trees and natural stone landscaping. A gravel driveway leads up to the entrance, where steps ascend to a covered porch. A dog is seen on the grassy area nearby.

Cottage in Cornwall

4.92 out of 5 average rating, 159 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Top guest favorite

An aerial view captures a sprawling farm landscape at sunset, with the sun dipping behind rolling hills. The guest house, white with a gray roof, is surrounded by green fields and lush vegetation, creating a serene atmosphere.

Farm stay in New Milford

5 out of 5 average rating, 119 reviews

Farm House

A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers we sell at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, chickens, barn cats and a resident farm dog, Finula. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

Guest favorite

An outdoor fire pit is surrounded by several adirondack chairs on a grassy area. A stone wall frames the fire pit, with trees and a glimpse of a secondary building in the background. The scene reflects a serene natural setting.

Cottage in Bethlehem

4.98 out of 5 average rating, 112 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

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.

Top guest favorite

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

4.99 out of 5 average rating, 111 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Guest favorite

A stone archway leads to a red barn-style house, framed by greenery and a variety of plants. The pathway is paved with stones, providing a natural ambiance. Small bistro tables and chairs are visible through the arch, creating a welcoming outdoor seating area.

Farm stay in Kent

4.87 out of 5 average rating, 324 reviews

(°) The Wandering Peacock (°)

The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

Top guest favorite

A comfortable living area is presented with a gray sofa adorned with decorative pillows. A wooden coffee table is positioned in front of the couch on a light-colored rug, while a floor lamp and a small side table add warmth to the space. A large window allows natural light to enhance the ambiance.

Apartment in Litchfield

4.97 out of 5 average rating, 124 reviews

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!

Top guest favorite

A view of a classic farmhouse, surrounded by green grass and trees. Hay is scattered across the foreground, and the house features a porch with visible outdoor seating. A quiet road is seen in the distance, offering a glimpse of the serene rural setting.

Home in Bethlehem

4.97 out of 5 average rating, 302 reviews

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.

Guest favorite

The interior space showcases exposed wooden beams and a bright, open layout. A comfortable seating area is positioned near large windows that provide natural light and views of the surrounding trees. A round dining table is visible, accompanied by a set of stylish chairs.

Home in Cornwall

4.92 out of 5 average rating, 272 reviews

Secluded modern forest cabin with private brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin