
Holiday rentals in Litchfield County
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Top-rated holiday rentals in Litchfield County
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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!

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

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.

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.

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!

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 Fiberoptic WiFi Smart TV 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

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.

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 inflatable two person kayaks are available for use from May 1 to November 1..

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!

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

Blackberry Cottage
Enjoy our peaceful (pet friendly) home, just a short drive to the center of Norfolk. Great for friends and/or family visits. Board games, puzzles and books inside for all; fire pit outside. Front & side decks, are perfect for relaxing. Access great cafes, shops & cultural delights in Norfolk. The nearby Ellen Battell Stoeckel Estate hosts Yale's Summer Chamber Music Concert series. It’s a home, not a hotel. I think you’ll love it!

Stuart Cottage/Minutes to Mohawk Ski Area
The Stuart Cottage is located on the grounds of the Mary Stuart House Bed and Breakfast. Owned by Mary and managed by Elizabeth, the cottage has one bedroom, wifi and plenty of charm...truly the perfect place to relax in a rustic, low-key location in the heart of the Litchfield Hills. Mohawk Mountain and Tyler lake are just a short car ride.
Popular amenities for Litchfield County holiday rentals
Other great holiday rentals in Litchfield County

The oldest home in Litchfield.

Fully Renovated Rural Barn

Halo Hollow Haus - Litchfield Lake & Ski Haven

Guesthouse at Bantam Woods - 2 bedrooms

The House on the Hill

Lake View Cottage

Bright & Airy Guest Suite

Litchfield Hills Lakefront Getaway!
Destinations to explore
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- Rentals with a washing machine and dryer Litchfield County
- Rentals with breakfast Litchfield County
- Rentals with a patio Litchfield County
- Rentals with a kayak Litchfield County
- Cabin rentals Litchfield County
- Farm stay rentals Litchfield County
- Waterfront rentals Litchfield County
- Guest house rentals Litchfield County
- Rentals with pools Litchfield County
- Fitness-friendly rentals Litchfield County
- Rentals with beach access Litchfield County
- Rentals with outdoor seating Litchfield County
- Rentals with a hot tub Litchfield County
- Beachfront rentals Litchfield County
- House rentals Litchfield County
- Cottage rentals Litchfield County
- Smoking-friendly rentals Litchfield County
- Private suite rentals Litchfield County
- Rentals with lake access Litchfield County
- Flat rentals Litchfield County
- Rentals with a fireplace Litchfield County
- Rentals with an EV charger Litchfield County
- Pet-friendly rentals Litchfield County
- Family-friendly rentals Litchfield County
- Rentals with a firepit Litchfield County
- Bed and breakfasts Litchfield County
- Yale University
- Six Flags New England
- Thunder Ridge Ski Area
- Fairfield Beach
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Taconic State Park
- Mohawk Mountain Ski Area
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Walkway Over the Hudson State Historic Park
- Storm King Art Center
- Yale University Art Gallery
- Sherwood Island State Park
- Ski Sundown
- Compo Beach
- Millbrook Vineyards & Winery
- Mount Southington Ski Area
- Naumkeag
- Poets' Walk Park
- Hudson Chatham Winery





