A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

Canaan Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Canaan vacation rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,158 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
The price is SAR 299
SAR 418 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Coffee/tea maker, fridge, microwave, oven

2. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is SAR 263
SAR 760 total
includes taxes & fees
29 Sep - 30 Sep
NEW RENO - Chalet-style farm loft near Tanglewood
TV, DVD player, books, video library

3. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is SAR 319
SAR 816 total
includes taxes & fees
29 Sep - 30 Sep
1800s Carriage house in Berkshires / Hudson Valley
Lobby

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,682 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is SAR 357
SAR 440 total
includes taxes & fees
30 Sep - 1 Oct
Vacation Village in the Berkshires
Exterior

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is SAR 743
SAR 1,645 total
includes taxes & fees
30 Sep - 1 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Property grounds

6. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is SAR 362
SAR 819 total
includes taxes & fees
29 Sep - 30 Sep
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior detail

7. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is SAR 852
SAR 2,023 total
includes taxes & fees
29 Sep - 30 Sep
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Exterior

8. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (178 reviews)
"Great little place."
United States
Kim
The price is SAR 371
SAR 415 total
includes taxes & fees
1 Oct - 2 Oct
Micosta Leisure Inn
Gift shop

9. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is SAR 362
SAR 819 total
includes taxes & fees
29 Sep - 30 Sep
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Property grounds

10. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is SAR 751
SAR 1,219 total
includes taxes & fees
29 Sep - 30 Sep
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Gift shop

11. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is SAR 362
SAR 819 total
includes taxes & fees
29 Sep - 30 Sep
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Coffee/tea maker, fridge, microwave, stovetop

12. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is SAR 661
SAR 1,988 total
includes taxes & fees
5 Oct - 6 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

13. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (18 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is SAR 469
SAR 688 total
includes taxes & fees
29 Sep - 30 Sep
Taborton Harvest Boulder Pines Cabin in the woods
Terrace/patio

14. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is SAR 935
SAR 1,139 total
includes taxes & fees
29 Sep - 30 Sep
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

15. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (63 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is SAR 368
SAR 497 total
includes taxes & fees
1 Oct - 2 Oct
All comforts of home
Coffee/tea maker, fridge, microwave, oven

16. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is SAR 338
SAR 524 total
includes taxes & fees
11 Oct - 12 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
House (3 Bedrooms) | Interior

17. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is SAR 841
SAR 2,081 total
includes taxes & fees
5 Oct - 6 Oct
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Outdoor dining

18. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is SAR 931
SAR 1,887 total
includes taxes & fees
29 Sep - 30 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
Indoor pool, a heated pool

19. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is SAR 362
SAR 819 total
includes taxes & fees
29 Sep - 30 Sep
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Pool

20. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is SAR 372
SAR 830 total
includes taxes & fees
29 Sep - 30 Sep
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Canaan Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Another great stay at VV. My hallway got flooded by a broken hot water heater on my first morning there (Friday), they got a property restoration co in to start cleanup right away but between the industrial fans blowing round the clock and stagnant odor from the soaked carpet hanging heavy all the way up and down the hall, if I hadn’t been checking out today (Sunday) I would have requested to move units for the rest of my stay. Staff was super professional, apologetic, this was not their fault, and I will happily book again at VV in the future."
Elizabeth 3-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

Frequently asked questions

Can I find vacation rentals in Canaan?

Yes, there are vacation rentals near popular points of interest in Canaan, or you can select a more secluded option if you want a relaxing place to stay. Canaan is known for its restaurants and coffeehouses. Make sure you have time to check out the shopping and local tours during your trip.

What's the top vacation rental in Canaan?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of Canaan is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Canaan?

Choose from 7 Expedia vacation rentals in Canaan for a memorable vacation.

What’s there to see and do in Canaan?

Queechy Lake and Hollow FIelds Reserve are a couple of lovely local spots to get outside and enjoy nature. Hand Hollow State Forest and Bates Memorial State Park are other places to visit while you're in town.

What’s a vacation rental in Canaan like?

Vacation rentals are private properties you can book for several days or longer in Canaan. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family getaway.