Deals on vacations and trips to Canaan

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Top Canaan hotels deals

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$177 nightly
The price is $198 total per night
$198 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Spa
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
Free Cancellation
$145 nightly
The price is $162 total per night
$162 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
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
Free Cancellation
$107 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road Litchfield CT
Free Cancellation
Reserve now, pay when you stay
$274 nightly
The price is $315 total per night
$315 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
A full-service spa and a 24-hour gym are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like cooked-to-order breakfast and free self parking.
Breakfast included
Spa
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2 out of 5
492 East Main St Torrington CT
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $109 total per night
$109 total
Dec 28 - Dec 29
Total with taxes and fees
A gym is featured at this motel, along with free self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A safe deposit box is provided and the front desk is staffed around-the-clock.
Breakfast included
Parking included
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
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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.

Popular places to visit

North Canaan Town Hall

North Canaan Town Hall is just one of the places to see in North Canaan, so why not enjoy the other things to explore during your travels?

North Canaan Town Hall

Eddy Field

Explore the great outdoors at Eddy Field, a lovely green space in North Canaan.

Eddy Field

Connecticut Railroad Historical Museum

You can spend time browsing the exhibits at Connecticut Railroad Historical Museum during your trip to North Canaan.

Connecticut Railroad Historical Museum

Frequently asked questions

How much are vacation packages to Canaan?
Packages, which include flights and hotels in Canaan, start from as low as . Make your travel fantasies come to life and secure your dream vacation with Travelocity today.
How long should my Canaan vacation be?
Many travelers spend about 3 nights in Canaan, but it's entirely up to you. If you hope to discover all the wonderful things this destination has waiting for you, why not hang around for a few extra nights?
Where can I get the best vacation package deals for Canaan?
No matter how you like to travel, Travelocity can help you get your hands on an unbeatable Canaan package deal. All you need to do is pick and choose between our 400 air carriers and 1,000,000 properties worldwide.
Why should I purchase my Canaan vacation package with Travelocity?
Whether you're in search of the ultimate unplugged vacation or you crave the hustle and bustle of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to search through countless websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available 24/7.
Can I save on my Canaan car rental if I bundle it with my hotel or flight?
With a Canaan vacation package, you can bundle your car, flight and hotel bookings and save tons. If you want to uncover the best of this fantastic location, why not head to Times Square? This famous sight is 95 mi from Canaan. With your own wheels, you'll be there before you know it.
Which airport is best for Canaan?
Many fly into Bradley Intl. Airport (BDL), 35 mi east of downtown Canaan. Others prefer Albany Intl. Airport (ALB) (55 mi away from central Canaan) or Tweed - New Haven Regional Airport (HVN) (55 mi away from central Canaan).
Where should I stay when visiting Canaan?
Many people opt to check in to the Villa Mariana Blackberry River. Luxury & renovated, comfort, peaceful nature.. It's an excellent base for your Canaan vacation.

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