Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

Adorable, storybook log cabin
SUPERHOST
Entire cabin · 9 guests · 5 beds · 2 baths
Adorable, storybook log cabinFantastic, authentic log cabin on 7 acres of wooded land with private pond that's good for a dip and with a sandy beach. Charm throughout with beds for nine to ten people.
Gateway to the Berkshires
SUPERHOST
Entire rental unit · 6 guests · 2 beds · 1 bath
Gateway to the BerkshiresRemodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.
Immaculate year-round lakefront at Highland Lake
SUPERHOST
Entire guesthouse · 7 guests · 4 beds · 2 baths
Immaculate year-round lakefront at Highland Lake"Lone Pine Cottage" Very special 3 bedroom / 2 full bath, 2016 ground-up restoration in Victorian cottage style. Magnificent in all four seasons. Desired direct waterfront spot on quiet east side cove. Perfect for couples or families. Kayaks, Canoe, sailboat. Central air, radiant heated floors, gas fireplace, washer/dryer, large deck with gas grill. Lawn area, good swimming area and dockage for you boat in front of the cottage. Strict no-pet and no-smoking inside the cottage policy

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Popular amenities for Winchester vacation rentals

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

Other great vacation rentals in Winchester

  1. Entire rental unit
  2. Winsted
Highland Lake 2nd Floor Duplex Blue Door Inn
$125 per night
  1. Entire residential home
  2. New Hartford
Lake House on the Cleanest Lake in CT
$250 per night
SUPERHOST
  1. Private room
  2. Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
$121 per night
  1. Entire serviced apartment
  2. Winsted
Haven at Highland lake
$85 per night
SUPERHOST
  1. Entire residential home
  2. Litchfield County
Meadow View House in Norfolk
$149 per night
SUPERHOST
  1. Entire residential home
  2. Winchester
Elegant waterfront home with peaceful sunset view
$400 per night
  1. Entire rental unit
  2. Barkhamsted
Farmington River house is an angler’s dream
$125 per night
SUPERHOST
  1. Private room
  2. Norfolk
Maple House, Berkshires Victorian: Birch Room
$160 per night
SUPERHOST
  1. Entire residential home
  2. Litchfield County
Litchfield County Home w/ a View + high speed wifi
$265 per night
SUPERHOST
  1. Private room
  2. Norfolk
Charming Village Colonial in the heart of Norfolk
$100 per night
SUPERHOST
  1. Entire residential home
  2. Winchester
Winchester House with wifi/high speed internet.
$240 per night
SUPERHOST
  1. Entire guest suite
  2. Winchester
Private Suite with Lake Views at Artist Residence
$175 per night