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

Canaan Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Canaan vacation 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, (1,161 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
$109 nightly
The price is $121
Oct 1 - Oct 2
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)
"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.
$204 nightly
The price is $207
Sep 30 - Oct 1
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.
$221 nightly
The price is $224
Sep 30 - Oct 1
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, (2,686 reviews)
"Love this place for a weekend getaway."
United States
Jacob
$122 nightly
The price is $136
Sep 30 - Oct 1
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.
$453 nightly
The price is $456
Oct 5 - Oct 6
Total with taxes and fees
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A snow-covered outdoor area with a fire pit, tables, and chairs.

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.
$202 nightly
The price is $226
Sep 30 - Oct 1
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern building with a wooden deck and a door.

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.
$602 nightly
The price is $674
Sep 30 - Oct 1
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

8. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (180 reviews)
"Great little place."
United States
Kim
$113 nightly
The price is $127
Oct 1 - Oct 2
Total with taxes and fees
Micosta Leisure Inn
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

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
$202 nightly
The price is $226
Sep 30 - Oct 1
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A camping setup with a metal chair and a table by a river in a forest.

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.
$305 nightly
The price is $342
Sep 30 - Oct 1
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

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.
$202 nightly
The price is $226
Sep 30 - Oct 1
Total with taxes and fees
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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.
$477 nightly
The price is $529
Oct 5 - Oct 6
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A wooden cabin with a porch, a door, and a window.

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.
$165 nightly
The price is $183
Sep 30 - Oct 1
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

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.
$292 nightly
The price is $329
Sep 30 - Oct 1
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
A wooden deck with a staircase leading to a covered porch area.

15. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (63 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
Oct 1 - Oct 2
Total with taxes and fees
All comforts of home
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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.
$125 nightly
The price is $140
Oct 11 - Oct 12
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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
$499 nightly
The price is $554
Oct 5 - Oct 6
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

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
$529 nightly
The price is $536
Sep 30 - Oct 1
Total with taxes and fees
NEW RENO Historic Creamery in Berkshires w/hot tub
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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.
$200 nightly
The price is $224
Sep 30 - Oct 1
Total with taxes and fees
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

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.
$202 nightly
The price is $226
Sep 30 - Oct 1
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Canaan Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Wonderful resort"
Ofer 2-night trip
Posted 9 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

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 $121 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.