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Choose from 987 Canaan Hotel Deals

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
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (752 reviews)
"Very good"

Reviewed on Oct 7, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,011 reviews)
A Great Weekend
"Room was comfortable and clean. The Inn is beautiful. We went to the Lions Den both evenings and had a drink and listened to live music. We couldn’t get a table at the restaurant but there are other good options in walking distance. The only disappointment was that the fireplace in our room was not ..."

Reviewed on Oct 12, 2025

The Red Lion Inn
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and 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 ...
8.2/10 Very Good! (1,007 reviews)
"Easy parking, good air air-conditioning."

Reviewed on Oct 10, 2025

Quality Inn
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! (672 reviews)
"Very clean room. Staff nice . Parking. Coffe machine lobby. Room has mini fridge and microwave and coffee/ tea machine. Comfortable bed. Much better than expected."

Reviewed on Oct 11, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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! (743 reviews)
"I would say 4.7 out of five stars. Clean friendly, very comfortable bed nice breakfast. My only complaint would be the toilet paper could be a better quality…"

Reviewed on Oct 9, 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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! (1,007 reviews)
"Excellent service!!!"

Reviewed on Oct 11, 2025

Quality Inn
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. ...
5.4/10 (764 reviews)
"We had 3 people staying in a room with two beds, though I registered for 4 people (the 4th canceled). We were a bit disappointed that there were so few towels, but when we asked, more were brought over promptly. The bagels at breakfast were really good toasted with whipped cream cheese. While it ..."

Reviewed on Oct 6, 2025

Americas Best Value Inn Torrington CT
The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road, Litchfield, CT
  • 50 min drive from North Canaan Town Hall
Stay at this 4-star 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! (947 reviews)
"Upscale. Clean and quiet."

Reviewed on Oct 7, 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! (1,011 reviews)
"Mold in bathtub. Outside: no one tends to the landscaping"

Reviewed on Oct 9, 2025

Days Inn by Wyndham Torrington
Blackberry River Inn

Blackberry River Inn

3 out of 5
538 Greenwoods Rd W, Norfolk, CT
  • 7 min drive from North Canaan Town Hall
Stay at this 3-star B&B in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (143 reviews)
"The highlight of our 10 day trip through the northeast"

Reviewed on Oct 12, 2025

Blackberry River 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! (767 reviews)
"Very convenient and we were happy that the little restaurant we'd chosen for dinner was right across the street (we drove anyway, as it's a busy street)."

Reviewed on Oct 13, 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 3-star hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount ...
9/10 Wonderful! (8 reviews)
"I had an absolutely amazing time here, it is even more beautiful than the pictures. Where do I begin! Right from the start we were greeted by welcoming staff who gave us a tour of the property on a golf cart as we reached our cabin. Golf carts are offered and easily available for a lift to anywhere ..."

Reviewed on Sep 27, 2025

Prospect Berkshires
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.

Find cheap hotels in Canaan

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Frequently Asked Questions About Canaan hotels

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How many hotels are there in Canaan?

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