House holiday rentals in Litchfield County

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Top-rated house rentals in Litchfield County

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Top Guest favourite
A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.
Home in Rhinebeck
4.98 out of 5 average rating, 130 reviews

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

Superhost
A charming red homestead is surrounded by a light coating of snow, with a wooden staircase leading to the entrance. Leafless trees are visible in the foreground, and a convenience store can be seen in the background, enhancing the house's accessibility.
Home in Torrington
4.88 out of 5 average rating, 128 reviews

Charming Home in Litchfield County on a MAIN ROAD!

Conveniently located on a MAIN ROAD in the heart of Torrington, this cozy homestead makes for the perfect New England getaway - seasonal activities to endure such as: hiking, swimming, kayaking, apple/pumpkin picking, skiing/snowboarding, and breweries & wineries. Close to Torrington’s historic downtown district featuring the Warner Theater & Kidsplay Museum. Conveniently located between a convenience store and some of Torrington’s finest coffee right next door from the Batchy Brew coffee truck.

Top Guest favourite
A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.
Home in Colebrook
4.99 out of 5 average rating, 246 reviews

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.

Top Guest favourite
A hot tub is illuminated with soft purple lights, positioned against a backdrop of trees. The distant lights of night skiing on the slopes create a vibrant atmosphere, enhancing the serene ambiance of the outdoor space.
Home in Cornwall
4.99 out of 5 average rating, 101 reviews

The Owl Cottage@Mohawk Mountain

**Less than 5 minute walk to Mohawk Ski Area.** 5 min drive to Mohawk Pond Snuggle up at "The Owl Cottage" Cute as can be with Natural, Romantic Charm. Enjoy the lights of night skiing from the **NEW HOT TUB** and outside fire pit. Newly renovated kitchen with gas stove. SMALL PETS considered 35 mins to Wassaic Train Station Great meeting spot between Boston & NYC Short Drive to: Mohawk Ski Area Mohawk Pond Covered Bridges Short drive to Kent, Litchfield, Washington, Great Barrington MA

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
4.82 out of 5 average rating, 456 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

Top Guest favourite
A newly remodeled kitchen showcases white cabinets complemented by a marble countertop and a decorative backsplash. A rustic wooden dining table with chairs is positioned near a window, while a vibrant area rug adds warmth to the space. Modern appliances are neatly integrated into the design.
Home in Salisbury
4.98 out of 5 average rating, 176 reviews

Under Mountain House

Our home is designed to be your home away from home! It has been newly renovated with comfort in mind so you can enjoy your stay in the Berkshires. Whether you are here to hike parts of the Appalachian Trail, stroll into town for a leisurely meal, enjoy Lime Rock Race Track or explore the many surrounding New England towns you can be assured you will always have a comfortable home to come back to!! My home is located just a 3 minute walk to the center of town and the historic White Hart.

Superhost
A charming three-story farmhouse is surrounded by lush greenery, featuring a welcoming front porch with seating. The design includes a shingled exterior and a pathway leading to the entrance, all set against a backdrop of vibrant trees.
Home in Sharon
4.9 out of 5 average rating, 230 reviews

Charming and relaxing 4b farmhouse group getaway

We are thrilled to share our idyllic country home with you and hope you enjoy it as much as we do. Built in 1882, set on a hill with ample indoor and outdoor space (two kitchens!) overlooking the Housatonic River and the famous West Cornwall bridge, our fully stocked house is close to hiking, fishing, kayaking, skiing/snowboarding. Set in gorgeous Litchfield Hills near the Appalachian trail, wineries, breweries, farms, rivers and lakes, waterfalls, antiques, casual or fine dining

Top Guest favourite
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
4.98 out of 5 average rating, 179 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 favourite
The living area features a light-colored sofa arranged with throw pillows, accompanied by a cozy armchair and a coffee table. Natural light floods through multiple windows, and a round mirror adds depth to the space. A door leads to the outdoor area, enhancing the room's connection to nature.
Home in Litchfield
4.98 out of 5 average rating, 255 reviews

Storybook Cape...HOST & Co.

Step back in time in this classic 1930s Cape Cod home, nestled in the serene beauty of the Litchfield Hills. Just a five-minute drive from the charming Litchfield Green, you’ll find antique shops, cozy cafés, unique boutiques, and a picturesque town center perfect for unwinding. Outdoor lovers will appreciate the proximity to the trails and wildlife of White Memorial Foundation, the peaceful beauty of Topsmead State Forest, and winter adventures at Mohawk Mt. Ski Area.

Top Guest favourite
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
4.98 out of 5 average rating, 328 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.

Top Guest favourite
A Craftsman-style home is surrounded by lush green lawns and gardens, featuring a warm, inviting facade. The structure includes a mix of gabled roofs and large windows, with a stone patio that presents outdoor seating. Copious trees provide natural shade, enhancing the tranquil setting.
Home in Litchfield
4.96 out of 5 average rating, 108 reviews

Home in historic Litchfield village

An enjoyable, easy 10 minute walk to the town center for shops & restaurants. A Craftsman Style home, it is casual & comfortable. Though private, we have neighbors that border our property. Guests best suited to our home would be small families or 2 or 3 couples looking for a very quiet small town getaway or a place to call home for a special event in the area. Please note 2 night minimum required and property to be used only by registered guests.

Guest favourite
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, 300 reviews

Tucked-away Charming Forest Cabin w/ 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

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