Sign up
Log in
Vacation rentals in Canaan

Vacation rentals in Canaan

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Canaan

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

  • *Freshly Renovated Studio-Breakfast Included*
    SUPERHOSTEntire guest house · 4 guests · 0 beds · 1 bathroom
    *Freshly Renovated Studio-Breakfast Included*

    130 five star reviews! Private, quiet, and ultra clean 550 sq. ft studio apartment. Offers bath, kitchenette, and private entrance over the garage (built in the 90s) of an 1800's Victorian farmhouse along historic Route 4. On Torrington's east side, home is set on 1 acre, nestled back from the road, and surrounded by mature trees and old stone walls from when the property was originally a dairy farm. Minutes to downtown, less than 45 minutes to Hartford, and about 2 hours to NYC.

    What guests are saying:

    “Amber's place was the best Airbnb I’ve ever stayed in. Not only was it full of thoughtful touches, it was beautifully and simply decorated and the cleanliness was next level. The apartment was in pristine condition as if we were the first guests ever. Their commitment to providing a 5 star accommodation is clear. We were quite busy during our visit so we didn’t speak or see our hosts but they were extremely responsive. Wouldn’t hesitate to stay again, I would move in if I could. Thank you!”

  • Cottage at Furnace Brook
    SUPERHOSTEntire guest house · 2 guests · 1 bed · 1 bathroom
    Cottage at Furnace Brook

    Come 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.

    What guests are saying:

    “Pam's cottage is truly charming, you won't be disappointed! My husband and I were just there for the night so we could ski at Mohawk Mountain the next day; it was perfect for us and only a few minutes from the mountain. Pam's communication was prompt and warm, her space full of personal touches and so welcoming, and our only complaint is we wish we could have stayed longer! The space is small but really all you need and very clean, the bed is comfortable and the sheets soft, and Pam and Walter have thought of and supplied so many amenities like toiletries, kitchen basics, and a binder full of local recommendations. Pam was also wonderful to communicate with and accommodating with logistics when we needed to arrive late. Check in and out was incredibly easy and to top everything off, the cottage is in a beautiful area with a river rushing by. Thanks Pam for everything!”

  • Stylish Berkshires Getaway
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    Stylish Berkshires Getaway

    Historic 1840s house with a modern vibe. Centrally located to all things Berkshires and the Hudson Valley. The sunny queen bedroom has a private attached bath. Stylish home with friendly hosts in a charming hamlet makes for a perfect country getaway. We want you to feel comfortable on your getaway. All linens, blankets, duvets, and surfaces are thoroughly cleaned and sanitized between each stay.

    What guests are saying:

    “Douglas and Danny’s space met and exceeded all of our expectations! It was absolutely gorgeous. Douglas has a fantastic eye for design. After a long day hiking, curling up on the couch in front of a fire and watching a movie was absolute perfection, as was sitting on the porch swing in the morning drinking tea. I loved that the breakfast and snack options were great before hiking (eggs, yogurt, oatmeal, trail mix), and my boyfriend loved the banana bread. Our room was a bit small (exactly as pictured) but had a HUGE closet so it was easy to keep tidy. We hardly wanted to spend time in the room when the house itself was so beautiful and cozy. We took Danny’s suggestions for dinners, which were great. We were 5 min walking from one more fun casual place and 8 min driving from a fancier lovely dinner. Lots of hikes, and bigger “cities” like Lee were also easy to get to. Great location overall.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Canaan holiday rentals

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

Other great vacation rentals in Canaan

Cozy Little  Cottage
SUPERHOSTEntire cottage
Cozy Little Cottage
Price:£90 / night
Bed and Bath in 1840's Greek Revival
SUPERHOSTPrivate room
Bed and Bath in 1840's Greek Revival
Price:£65 / night
Clean & Comfortable Older Cape w/ cat
Private room
Clean & Comfortable Older Cape w/ cat
Price:£33 / night
Stylish Berkshires Getaway
SUPERHOSTPrivate room
Stylish Berkshires Getaway
Price:£49 / night
*Freshly Renovated Studio-Breakfast Included*
SUPERHOSTEntire guest house
*Freshly Renovated Studio-Breakfast Included*
Price:£73 / night
Gardens Galore and Village Whimsy Retreat
SUPERHOSTEntire flat
Gardens Galore and Village Whimsy Retreat
Price:£72 / night
Maple House, Berkshires Victorian: Oak Room
Private room
Maple House, Berkshires Victorian: Oak Room
Price:£77 / night
Rustic Farmhouse; Cozy Suite; Litchfield County
SUPERHOSTEntire guest suite
Rustic Farmhouse; Cozy Suite; Litchfield County
Price:£55 / night
Rural small cabin  with river view and access
Entire cottage
Rural small cabin with river view and access
Price:£57 / night
Cornwall Colonial w/ Double Bedroom
SUPERHOSTPrivate room
Cornwall Colonial w/ Double Bedroom
Price:£69 / night
Walk to Brewery in Historic Railroad Depot
Entire guest suite
Walk to Brewery in Historic Railroad Depot
Price:£65 / night
Downtown Kent style & comfort! Upstairs 1 Bdrm apt
SUPERHOSTEntire flat
Downtown Kent style & comfort! Upstairs 1 Bdrm apt
Price:£85 / night
Show all