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Holiday rentals in Litchfield County

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Top-rated holiday rentals in Litchfield County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage at Furnace Brook
SUPERHOST
Entire guest house · 2 guests · 1 bed · 1 bathroom
Cottage at Furnace BrookCome enjoy our cozy, clean, newly renovated semi-detached cottage in the Litchfield Hills. Stay in, cook dinner, and relax on the large porch and listen to the sound of our brook and the Housatonic River just steps away. An ideal writer or artist retreat. Or enjoy the surrounding area - there are lots of restaurants, galleries, day hikes, and outdoor activities within a short drive. 8 miles to Kent, voted the prettiest small town in CT, 5 miles to Mohawk Ski Area and 20 minutes to Metro North.
Cottage on Babbling Brook
Entire cabin · 6 guests · 5 beds · 1 bathroom
Cottage on Babbling BrookCozy, Rustic Cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. A great space for families and friends. Conveniently located on the CT/NY border, just a 1 ½ hour drive or metro north from NYC, the area is a prime location for many reasons. It offers some of the most stunning and scenic drives in the country.
Newly Listed. Litchfield country escape
Entire residential home · 7 guests · 4 beds · 2.5 bathrooms
Newly Listed. Litchfield country escapeNewly Listed 3 bedroom contemporary house . Master bedroom setup with crib, king bed and single bed. Natural light throughout the house . Large private deck at back of house . Full home office setup with peloton bike , computer monitor, keyboard, mouse and printer. High speed internet. Fully equipped kitchen. Washer dryer in finished basement . 3 miles from historic Litchfield village with Sunset Meadow vineyard less than a mile walk. Multiple hiking trails at White Memorial Conservation Center

Holiday rentals for every style

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Popular amenities for Litchfield County holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Litchfield County

  1. Entire cottage
  2. Sharon
You deserve a peaceful time in the country
$114 SGD per night
SUPERHOST
  1. Entire residential home
  2. Litchfield
Rustic Fully Renovated Private House w/ Hot Tub
$269 SGD per night
  1. Entire residential home
  2. New Milford
Lakefront w/ private dock & beautiful sunsets!
$1,143 SGD per night
SUPERHOST
  1. Entire cabin
  2. Canaan
Your Cabin Away From Home
$572 SGD per night
SUPERHOST
  1. Entire cottage
  2. Goshen
Stuart Cottage...HOST & Co.
$262 SGD per night
  1. Entire residential home
  2. Colebrook
Stylish Comfort in a Stunning Setting
$716 SGD per night
SUPERHOST
  1. Entire guest house
  2. Winchester
Immaculate year-round lakefront at Highland Lake
$303 SGD per night
SUPERHOST
  1. Entire cottage
  2. Collinsville
The Carriage House
$168 SGD per night
SUPERHOST
  1. Entire guest suite
  2. Sherman
Guesthouse w KAYAKS, BIKES, & passes to LAKE beach
$182 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Kent
Kent Village Toll House
$148 SGD per night
SUPERHOST
  1. Entire residential home
  2. Litchfield
Storybook Cape...HOST & Co.
$436 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Litchfield
Perfect, peaceful retreat
$174 SGD per night