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Choose from 992 Canaan Hotel Deals

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
  • 42 min drive from North Canaan Town Hall
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
I had always wanted to stay at The Red Lion Inn and decided to treat myself to a one-night stay. Since it was in December I was especially excited to have a fireplace in the room. Sadly, I learned the fireplace didn’t work and that they are renovating some of the systems, but offered no partial refund ...

Reviewed on Dec 23, 2025

The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
  • 41 min drive from North Canaan Town Hall
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9/10 Wonderful! (806 reviews)
very good stay my only recommendation would be to have more coffee supplies as their is only enough for one pot of coffee and we were staying two days other than that very peaceful and comfortable.

Reviewed on Dec 22, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road Litchfield CT
  • 50 min drive from North Canaan Town Hall
Book a stay at this spa hotel in Litchfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition ...
9/10 Wonderful! (963 reviews)
A delightful stay from beginning to end - clean, bright, beautiful in a lovely are of the state.

Reviewed on Dec 14, 2025

The Litchfield Inn
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2 out of 5
492 East Main St Torrington CT
  • 41 min drive from North Canaan Town Hall
Book a stay at this business-friendly motel in Torrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,004 reviews)
Room very clean. Great temperature, comfortable bed.

Reviewed on Dec 22, 2025

Days Inn by Wyndham Torrington
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
  • 30 min drive from North Canaan Town Hall
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (710 reviews)
The room was super clean and comfortable. Nice television and great bathroom. Highly recommend!

Reviewed on Dec 21, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
  • 27 min drive from North Canaan Town Hall
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,001 reviews)
My go to place for my ski weekends

Reviewed on Dec 20, 2025

Quality Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd Great Barrington MA
  • 29 min drive from North Canaan Town Hall
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (758 reviews)
Yes

Reviewed on Nov 21, 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

2.5 out of 5
395 Winsted Rd Torrington CT
  • 38 min drive from North Canaan Town Hall
Book a stay at this business-friendly hotel in Torrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
5.6/10 (781 reviews)
It was a good we spent time together so go ahead- keep-up Thanks

Reviewed on Nov 15, 2025

Americas Best Value Inn Torrington CT
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street Lee MA
  • 45 min drive from North Canaan Town Hall
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,003 reviews)
No real problems. Great price. Easy access to I-90. Nice, walkable town with several nearby restaurants.

Reviewed on Dec 22, 2025

Quality Inn
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
  • 29 min drive from North Canaan Town Hall
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
8.8/10 Excellent! (810 reviews)
Clean, cozy and reasonably priced. Our favorite stay in GB! Within walking distance of many good restaurants, MMM provides a mini fridge and microwave for leftovers and a table for two to enjoy them later - not often found in even more pricey stays.

Reviewed on Dec 22, 2025

Monument Mountain Motel
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
  • 28 min drive from North Canaan Town Hall
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area ...
9.4/10 Exceptional! (15 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

Prospect Berkshires
the Alander

the Alander

2.5 out of 5
7519 NY-22 Copake NY
  • 15 min drive from North Canaan Town Hall
Stay at this lodge in Copake. Enjoy free WiFi, free parking, and rainfall showerheads. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (190 reviews)
Always a fun stay

Reviewed on Dec 5, 2025

the Alander
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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