Photo by Robin/Loving Life

Search Resorts in Canaan

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare Resorts in Canaan with updated reviews, rates, and availability.

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Room

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

8.6 out of 10, Excellent, (8)
"Great place to stay very clean and comfortable."
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Exterior

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
SKI SLOPE on the property. It is walkable to our cabin. But a car will be easier

SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!

9.6 out of 10, Exceptional, (15)
"Kim is a wonderful host, and her cabin is just perfect. This is my second time staying at her place, since I like to travel with my dog whenever possible. Very roomy with a high ceiling, but still nice and toasty. It has everything you could want in a full kitchen, and there’s also a great restaurant and country store/deli just a few steps away. We had a great time at the haunt this Halloween season, which I had never done before. Lots of fun things to do, and gorgeous hikes in the area. I have...
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Exterior

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was beautiful. We had a great stay"
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Pool

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

10.0 out of 10, Exceptional, (1)
"We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Snow and ski sports

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

10.0 out of 10, Exceptional, (2)
"This property is great for skiing, especially with kids. There is a nice pool and little movie theater thats prefect for after a day on the slopes."
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Snow and ski sports

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

10.0 out of 10, Exceptional, (3)
"We enjoyed the condo. Has everything that we needed and we were able to walk to the mountain in 5 minutes. Clean condo and clean white bedding. Plenty of towels and pool towels. "
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
Bedroom with king bed and ensuite bathroom.

Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires

2.0 star property
10.0 out of 10, Exceptional, (2)
"We enjoyed staying at this clean, quiet, and comfy property. Close to so many beautiful spots! Only minutes to both New York and Vermont!"
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Snow and ski sports

Pres Week- Bentley Brook Resort - Your Peak Winter Escape

10.0 out of 10, Exceptional, (1)
"Great location and overall wonderful stay at Jiminy Peak!"
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Exterior

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Snow and ski sports

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

10.0 out of 10, Exceptional, (3)
"These units are convenient, clean and spacious.We had the two bedroom/two bathroom & it was perfect for our family. So close to the mountain and restaurants too. "
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Snow and ski sports

Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

10.0 out of 10, Exceptional, (2)
"The property manager was great and very communicative. The hotel is the perfect place to stay if skiing at Jiminy peak. Ski school right outside, pool and arcade room for the children."
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
Exterior

Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort

Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
Vacation Village In The Berkshires 5 Star Resort - Suite B
Exterior

Vacation Village In The Berkshires 5 Star Resort - Suite B

Vacation Village In The Berkshires 5 Star Resort - Suite B
Slope-Side Ski-in Ski-Out: Bentley Brook Resort
Wyndham Bentley Brook Resort

Slope-Side Ski-in Ski-Out: Bentley Brook Resort

Slope-Side Ski-in Ski-Out: Bentley Brook Resort
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Exterior

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl

10.0 out of 10, Exceptional, (1)
"Large property with ski-in/ski-out proximity to Jiminy Peak. Units are standard but large, clean, and with helpful amenities for a family vacation (kitchenette in unit, plus nice pool for kids' apres-ski, kids' movies, etc.) We'll be back."
Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Snow and ski sports

Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss

10.0 out of 10, Exceptional, (1)
"Walked out of the building, straight into my kids skiing lessons, very convenient."
Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Snow and ski sports

Hot SKI-in SKI-out Rentals Bentley Brook Resort!

10.0 out of 10, Exceptional, (1)
"Great property! Great location. Smooth check-in."
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Snow and ski sports

Jiminy Premier Ski-In/Ski-Out Resort Bentley B

10.0 out of 10, Exceptional, (2)
"Fun time. Conditions were good. We love this family Mountain "
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Snow and ski sports

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
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.
Don't see what you're looking for?
See all available properties in Canaan
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Canaan

Vacation Village in the Berkshires
Exterior

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is AED 529
AED 617 total
includes taxes & fees
14 Feb - 15 Feb
Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AED 879
AED 981 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 694
AED 762 total
includes taxes & fees
10 Feb - 11 Feb
Jiminy Peak Mountain Resort
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.

Frequently asked questions

What can I expect from a resort vacation in Canaan?
You deserve a getaway, and a resort is just the place to indulge in all the services and amenities you need for a relaxing time in Canaan. One of the comfortable resorts in the area could be just what you’re searching for, whether you want an amazing pool, shopping possibilities, or activities for the kids.
What's a favorite resort in Canaan?
Our highest-rated resorts around Canaan: SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires! - Ski resort right by Jiminy Peak Mountain Resort. 12.7 mi (20.5 km) from Canaan. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort steps from Jiminy Peak Mountain Resort. 12.8 mi (20.5 km) from Canaan. Amenities include ski-in/ski-out access, a fitness center, and a garden. All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Only a 5-minute walk from Jiminy Peak Mountain Resort. 12.9 mi (20.7 km) from Canaan. Access to a sauna.
What can I do in Canaan?
Queechy Lake, Hollow FIelds Reserve, and Hand Hollow State Forest are a few of the interesting sights to visit. Other attractions in the area include Bates Memorial State Park and Hancock Shaker Village.
What's the weather like in Canaan?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Canaan?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 8 mi (12.9 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 15.8 mi (25.4 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.