Cottage vacation rentals in Litchfield County

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Top-rated cottage rentals in Litchfield County

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Guest favorite

Cottage in Falls Village

4.99 out of 5 average rating, 105 reviews

Forest Retreat w Tennis, Swim Pond and Waterfalls

Perched above a brook in the woods. See the seasons fold and unfold in 50 acres of private forest, waterfalls, & pond. Fall asleep to sounds of the creek below. Wake to a canopy of beams, dappled sunshine, breakfast on a screened porch. Respite, creativity, and play (tennis/basketball/swim/hike). Hand built by Jacques Beckwith, inspired by Japanese teahouses, featuring tongue & groove construction, shoji screen doors, & tatami mats. YouTube or IG video, search "Cornwall Hollow Teahouse"

Guest favorite

Cottage in Cornwall

4.94 out of 5 average rating, 132 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.

Guest favorite

Cottage in Harwinton

4.97 out of 5 average rating, 34 reviews

Newly renovated 2 bedroom cottage on the lake!

Come relax by the lake! Peaceful, rejuvenating, and lots of fun on one of the cleanest lakes in CT. No gas engines allowed on the water, which ensures a peaceful stay. The beach is just 30 seconds away. Enjoy water views from the front yard and chill out in the evening at the fire pit. The owner lives just down the road and you're invited to use his kayak and canoe. The cottage is newly renovated, with a completely updated bathroom. Lots of windows and great light. Come enjoy!

Guest favorite

Cottage in Goshen

4.95 out of 5 average rating, 119 reviews

Country Cottage in Goshen

Quaint country cottage, with beautiful hardwood floors, screened in porch, claw foot bathtub and lots of antiques set on a naturally landscaped 1 acre property. The original cottage was built in 1932, but was completely renovated in the last 5 years. 650 square feet with a bedroom, bathroom, lounge on the 2nd floor loft, and an open floor plan with living area, dining area and kitchen on the first floor. French doors lead from the dining area to a large screened in porch.

Guest favorite

Cottage in Bethlehem

4.99 out of 5 average rating, 82 reviews

Cozy Cottage in Litchfield Cty | Pet Friendly

The Cottage at The Grove is the perfect place to escape, the fall foliage surrounds the cabin and provides a peaceful setting. The Cottage features a wood burning stove & outdoor fire pit. It is well equipped with everything you will need for your stay from a fully stocked kitchen to bath salts for the deep soaking tub. Minutes to March Farms, a must for fall activities. For security we have two exterior cameras facing the door & driveway. Escape to Litchfield County!

Guest favorite

Cottage in Sharon

5 out of 5 average rating, 16 reviews

Comfortable cottage surrounded by nature

Enjoy a peaceful stay in this quiet and cozy two-bedroom cottage surrounded by nature. Relax by the fire pit amidst apple trees while listening to the sound of the brook. Local outings include: a pick-your-own apple and fruit orchard next door; the Audubon center down the road for nature tours; the Housatonic River, Appalachian Trail and several other beautiful hikes less than a mile away; dining and shopping in nearby Sharon, Millerton, Kent and Great Barrington.

Guest favorite

Cottage in Litchfield

4.89 out of 5 average rating, 304 reviews

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

Guest favorite

Cottage in North East

4.86 out of 5 average rating, 148 reviews

Sunset Cottage: Unplug - Relax - Recharge

Charming country cottage in Millerton, New York with a variety of nearby destinations. Unwind on a quiet country road with cows as your closest neighbors. Use as a base to explore the Tri-State area. Perfect for Parent Weekends for the nearby private schools. An idyllic setting in which to unplug and enjoy nature. Walk to the 42-mile Rail Trail, strap your bikes, skis, kayaks, or canoes to the car because you’ll be centrally located for adventure!

Superhost

Cottage in South Kent

4.8 out of 5 average rating, 191 reviews

Lake View Cottage in Kent, CT

Kent, CT is the place to be if you enjoy the outdoors; hiking, birding, kayaking, fishing, biking and walking as the scenery is beautiful. There is much to explore; gardens, farms and wineries/distilleries/breweries. This northwest corner of CT in the Litchfield Hills is a magical, laid back area of New England where you will find neighborhood bars, not clubs. Enjoy low key restaurants with gourmet food or cook at home with farm fresh ingredients.

Guest favorite

Cottage in Sharon

4.92 out of 5 average rating, 154 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

Enjoys luxurious Get away to lovely Sharon, CT, just 2 hours from NYC/3 hours from Boston. Enjoy a chill vibe, garden and mountain views, and fresh organic eggs from our lovely flock of hens. We’ve created a luxurious and spacious modern feel, in a bucolic farmland setting. All newly refurbished with a luxurious modern bath with rain shower and fabulous marble stone work. Coyuchi bedding, soft organic cotton linens, and gourmet kitchen!

Guest favorite

Cottage in Kent

5 out of 5 average rating, 53 reviews

Cheerful one-bedroom cottage with large porch

This charming one bedroom, one bath cottage is perfect for two people and has everything to keep you comfortable. The cottage overlooks a natural spring pond and has a very large deck to enjoy morning coffee or afternoon sun. It is 5 minutes from the town of Kent and centrally located to many parks and lakes. Absolutely beautiful area. Caretaker lives in the main house next to cottage. Located 2-hrs from NYC.

Guest favorite

Cottage in New Fairfield

4.94 out of 5 average rating, 266 reviews

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

Charming waterfront 4 Bedroom / 2 BA house on Candlewood lake with private dock and toys. Lake living at its best out your back door. Great yard and updated house for hosting family & friends. Turn Key vacation ~75 minutes / 60 miles from NYC. Screened in Porch, Backyard Patio w/ firepit, Grill and more. Well stocked house with full kitchen, TONS of movies & entertainment, and more.