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Holiday rentals in Canaan

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Top-rated holiday rentals in Canaan

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

Modern studio with views of the treetops
Entire guest house · 4 guests · 2 beds · 1 bathroom

Modern studio with views of the treetopsOur Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a brand new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Year Round Serenity at the Bird Cottage
SUPERHOST
Entire guest house · 2 guests · 1 bed · 1 bathroom

Year Round Serenity at the Bird CottagePeaceful, private and comfortable stay in the country close to local attractions. This guest cottage is in a serene setting just 5 miles north of downtown Chatham in the heart of horse country. Set on 7 acres with two ponds there is ample room to roam and relax. Apartment has a queen size bed, TV, internet, AC, mini fridge, Keurig coffee maker, and microwave. Quick access from the Taconic and I-90 make getting here easy. Short drive to Chatham or Valatie for charming stores and restaurants.

Brand New Guest Suite in Old Chatham Hunt Country
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bathroom

Brand New Guest Suite in Old Chatham Hunt CountryLooking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

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Popular amenities for Canaan holiday rentals

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

Other great holiday rentals in Canaan

SUPERHOST
  1. Entire guest suite
  2. Chatham
The Inn at Chatham - Romantic getaway
SUPERHOST
  1. Entire house
  2. West Stockbridge
Sweet Escape with Indoor Pool and Panoramic Views
SUPERHOST
  1. Entire cottage
  2. Valatie
Escape to the lake- kayak, swim, relax, unwind
  1. Entire house
  2. Canaan
Country Cottage
SUPERHOST
  1. Private room
  2. Pittsfield
Equestrian retreat
  1. Entire house
  2. Chatham
Cozy Nordic-styled cabin w/river view in village
SUPERHOST
  1. Entire flat
  2. New Lebanon
Sunny Duplex at the old boarding house
SUPERHOST
  1. Entire guest house
  2. Lenox
Lenox - Sunny cottage nestled in the garden
SUPERHOST
  1. Entire cabin
  2. Canaan
Newly Renovated Cabin in the Country
SUPERHOST
  1. Tiny house
  2. Nassau
HGTV Tiny Home☀️2 hrs NYC🌲Quiet Oasis⚡️WIFI✨Clean
SUPERHOST
  1. Entire cottage
  2. West Stockbridge
Cozy Stockbridge Cottage
SUPERHOST
  1. Entire cottage
  2. New Lebanon
The Writer's Cottage

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