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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.

1 bedroom suite with full bath & separate entrance
Private room · 2 guests · 1 bed · 1 private bathroom

1 bedroom suite with full bath & separate entranceA completely renovated farmhouse built in 1900. Beautiful landscaped gardens and sitting areas located in the backyard. Backyard amenities include a patio, fire pit, hammock and picnic table. Self-check in to private entrance and stairs leading to second floor which includes a master bedroom with queen-sized bed, living room/dry kitchenette with mini fridge and large full bath with both shower and tub options. Air conditioning, Wi-Fi and smart TV on site.

Loft in the Pines
Entire guest house · 4 guests · 2 beds · 1.5 bathrooms

Loft in the PinesLoft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY and Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking and skiing. Easy walk to antique shops, the Music Cellar and delicious restaurants or put your feet up and relax! There are 1.5 baths, a living room with flat screen TV, dining room and a fully equipped kitchen with an expansive deck to take in the view.

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.

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

SUPERHOST
  1. Entire cabin
  2. Cornwall
Country Cabin by the lake
₹13,016 per night
SUPERHOST
  1. Entire guest suite
  2. Morris
Lakeside Private Guest Suite
₹6,297 per night
  1. Entire cottage
  2. Sharon
Quiet West Cornwall cottage with river view/access
₹7,778 per night
SUPERHOST
  1. Entire guest suite
  2. Warren
Rustic Farmhouse; Cozy Suite; Litchfield County
₹5,111 per night
SUPERHOST
  1. Entire cabin
  2. New Fairfield
The Little Lake Cabin - near lake with hot tub
₹15,557 per night
SUPERHOST
  1. Entire guest house
  2. Roxbury
Transylvania Guest House - A woodland retreat
₹11,112 per night
SUPERHOST
  1. Entire guest house
  2. Canaan
Clean, quiet garage apartment with large deck
₹11,112 per night
SUPERHOST
  1. Entire guest suite
  2. Sherman
Relaxing lake-view retreat
₹9,260 per night
SUPERHOST
  1. Entire house
  2. Canaan
Litchfield County Retreat
₹6,911 per night
  1. Entire cottage
  2. New Milford
Riverfront Cottage Delight-
₹9,260 per night
SUPERHOST
  1. Entire cabin
  2. Sherman
The Cove Cabin
₹36,669 per night
  1. Entire guest house
  2. Canton Center
Treehouse retreat set in old forest
₹5,852 per night

Top-rated things to do in Litchfield County

Unique activities hosted by local experts vetted for quality