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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Canaan vacation rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,233 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
$115 nightly
The price is $128
Nov 25 - Nov 26
Total with taxes and fees
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
8.6 out of 10, Excellent, (7 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.
$203 nightly
The price is $206
Oct 28 - Oct 29
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

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.
$222 nightly
The price is $225
Nov 5 - Nov 6
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,799 reviews)
"We had an amazing stay."
United States
Luke
$128 nightly
The price is $143
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A white two-story house with a porch, surrounded by trees and a hill.

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.
$430 nightly
The price is $436
Nov 9 - Nov 10
Total with taxes and fees
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

6. 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.
$219 nightly
The price is $233
Oct 28 - Oct 29
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

7. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (192 reviews)
"Great stay"
United States
George
$113 nightly
The price is $127
Nov 1 - Nov 2
Total with taxes and fees
Micosta Leisure Inn
A bedroom with a wooden bed, a window with a view of trees, and a red chair.

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
$166 nightly
The price is $184
Oct 28 - Oct 29
Total with taxes and fees
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A Country Inn with a large, welcoming entrance and a parking area.

9. 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, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
$200 nightly
The price is $224
Oct 28 - Oct 29
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

10. 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.
$200 nightly
The price is $224
Oct 28 - Oct 29
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A lobby with leather sofas, a fireplace, and a stone wall.

11. 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
$200 nightly
The price is $224
Oct 28 - Oct 29
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

12. 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.
$200 nightly
The price is $224
Oct 28 - Oct 29
Total with taxes and fees
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Exterior

13. 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, (16 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.
$305 nightly
The price is $342
Oct 28 - Oct 29
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

14. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"Great location! "
United States
shannon m.
$200 nightly
The price is $224
Oct 28 - Oct 29
Total with taxes and fees
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
A wooden cabin with a porch, a door, and a window.

15. 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
$153 nightly
The price is $169
Oct 28 - Oct 29
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

16. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
$200 nightly
The price is $224
Oct 28 - Oct 29
Total with taxes and fees
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A cozy living room with a sofa, a fireplace, and large windows.

17. 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.
$607 nightly
The price is $679
Oct 28 - Oct 29
Total with taxes and fees
Luxury Barn Near Hudson With New Private Sauna
A wooden deck with a staircase leading to a covered porch area.

18. 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
$118 nightly
The price is $132
Nov 1 - Nov 2
Total with taxes and fees
All comforts of home
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

19. 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)
"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.
$134 nightly
The price is $150
Nov 3 - Nov 4
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern building with a wooden deck and a door.

20. 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.
$625 nightly
The price is $700
Oct 28 - Oct 29
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
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
"Great"
Anna 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about Canaan

Everything you need to know about Canaan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Canaan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Canaan vacation 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 low season months. For more hustle and bustle, you may prefer to visit Canaan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Canaan rentals

At Expedia, we put the best Canaan vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.