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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Canaan holiday rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,268 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is £81
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is £152
includes taxes & fees
16 Nov - 17 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A gazebo with a stone floor and a grassy area with trees in the background.

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 £161
includes taxes & fees
22 Nov - 23 Nov
1800s Carriage house in Berkshires / Hudson Valley
Indoor pool

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,841 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is £75
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

5. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (197 reviews)
"Great stay"
United States
George
The price is £67
includes taxes & fees
16 Nov - 17 Nov
Micosta Leisure Inn
A white two-story house with a porch, surrounded by trees and a hill.

6. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (6 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 £310
includes taxes & fees
18 Nov - 19 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A porch with two Adirondack chairs, a welcome mat, and a door labeled "Apartment 2".

7. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is £162
includes taxes & fees
15 Nov - 16 Nov
Berkshires Apartment at the Stephentown Hotel
A wooden bed in a room with a sloped ceiling and a window overlooking a forest.

8. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
10.0 out of 10, Exceptional, (1 review)
"The cabin was just what we needed! A gorgeous fall day, trees only visible from the window. The cabin had a comfortable bed, plenty of blanket and a chair. A rocker was on the porch. From this cabin, you turn right from the door and walk straight to the Bessie Woods trail. The common area had everything we needed, clean, comfortable. If you want to relax, this is pretty special!"
United States
Trena
The price is £133
includes taxes & fees
13 Nov - 14 Nov
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A modern building with a wooden deck and a door.

9. 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 £433
includes taxes & fees
16 Nov - 17 Nov
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious living room with wooden beams, large windows, a chandelier, and a fireplace.

10. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is £496
includes taxes & fees
18 Nov - 19 Nov
Luxury Barn Near Hudson With New Private Sauna
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is £88
includes taxes & fees
18 Nov - 19 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A camping setup with a metal chair and a table by a river in a forest.

12. 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, (18 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 £244
includes taxes & fees
6 Dec - 7 Dec
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden cabin with a porch and multiple windows.

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, (20 reviews)
"Good location for sightseeing around the north east and New England"
United States
Nathan
The price is £122
includes taxes & fees
13 Nov - 14 Nov
Taborton Harvest Boulder Pines Cabin in the woods
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

14. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is £162
includes taxes & fees
15 Nov - 16 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A fire pit with chairs, a ski lift, and a building with a sign that reads "Mountain Resort".

15. 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 £162
includes taxes & fees
15 Nov - 16 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A cozy living room with a large window, wooden walls, and a television.

16. 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 £162
includes taxes & fees
15 Nov - 16 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

17. 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, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is £172
includes taxes & fees
16 Nov - 17 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

18. 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 £440
includes taxes & fees
16 Nov - 17 Nov
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A snow-covered outdoor area with a fire pit, seating, and a building in the background.

19. 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 £162
includes taxes & fees
15 Nov - 16 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A wooden deck with a staircase leading to a covered porch area.

20. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (65 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is £94
includes taxes & fees
23 Nov - 24 Nov
All comforts of home
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

A red building with a sign reading "Shaker Mill Inn".
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
West Stockbridge

10/10 Excellent

Super self contained room, welcoming hosts and good meal at the Shaker Inn restaurant next door. Lovely little town. Coffee at #6 in old railway station in town a must.
United Kingdom
Ian
Reviewed September 22, 2018
Shaker Mill Inn

Find out more about Canaan

Everything you need to know about Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Canaan holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Canaan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Canaan. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Canaan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Canaan holiday rentals we have selected for you start as low as £66 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Canaan rentals

At Expedia, we put the best Canaan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Canaan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Canaan?

Yes, there are holiday rentals close to the most popular sights in Canaan, or you can select a more secluded option if you're looking for a relaxing stay. Canaan is known for its restaurants and coffee shops. Make sure you have time to check out the shopping and local tours during your trip.

What are some of the best holiday rentals that Canaan has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Canaan is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Canaan?

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

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 holiday rental in Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Canaan. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.