Book Exclusive Canaan Vacation Packages

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Top Canaan hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is CA $143 per night
CA $143
CA $175 total
Dec 15 - Dec 16
includes taxes & fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Parking included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $103 per night
CA $103
CA $115 total
Dec 24 - Dec 25
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Guido's Marketplace and Bousquet Ski Area are located nearby.
Pool
Hot tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free cancellation
The price is CA $128 per night
CA $128
CA $143 total
Dec 16 - Dec 17
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $136 per night
CA $136
CA $183 total
Jan 8 - Jan 9, 2026
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead are located nearby.
Pool
Hot tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $151 per night
CA $151
CA $169 total
Dec 14 - Dec 15
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kennedy Park and Pleasant Valley Wilderness Sanctuary are located nearby.
Pet-friendly
Parking included
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
The price is CA $197 per night
CA $197
CA $282 total
Jan 12 - Jan 13, 2026
includes taxes & fees
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. Popular attractions Schantz Galleries and Mission House are located nearby.
Pool
Spa
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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

Queechy Lake

Commune with nature and explore the great outdoors at Queechy Lake during your travels in Canaan. Discover the area's museums and shops.

Queechy Lake

Canaan Vacations

Get your vacation off to the best start possible by knowing a thing or two about Canaan before you head off.

This neighborhood sits 25 miles (40 kilometers) to the southeast of the center of Albany, the state capital of New York.

The population of Albany is roughly 98,000.

Places to visit in Canaan

Venture into the wider Albany region and get closer to nature with some activities like snowboarding. If you really want to create some special vacation memories, stick skiing on your must-do list as well.

Where do you fly into for Canaan?

Arriving at Bradley International Airport (BDL)? Get through security, exit the terminal and you'll be 50 miles (80 kilometers) to the southeast from the heart of Canaan.

Frequently asked questions

How much are vacation packages to Canaan?
Your vacation fantasies can be realized in Canaan for as low as . Our affordable package deals include flights and hotels, so organizing your itinerary will be a piece of cake. The only thing you'll need to focus on is what amazing attraction you'll head to first.
How long should my Canaan vacation be?
Many travelers like to spend around 2 nights in Canaan. But what's right for them mightn't be right for you. Whether you opt to stay for a few days or a few weeks, you'll love exploring all the fantastic things that this place has to offer.
Where can I get the best vacation package deals for Canaan?
You can snap up fantastic Canaan package deals with Travelocity. Mix and match from as many as 400 partner airlines and 1,000,000 properties worldwide and turn those travel dreams into a reality.
Why should I purchase my Canaan vacation package with Travelocity?
Because we believe in creating stress-free vacation experiences. From hotels and flights to car rentals and activities, we put everything at your fingertips. Our customer support is available 24/7 to make sure your needs are taken care of. We also offer a Price Match Guarantee, so you can secure your vacation knowing you've scored the best deal possible. How? If you find a lower price, we'll match it!
Will I save money on my Canaan car rental if I bundle it with hotels and flights?
Bundling your car, flight and hotel into a Canaan vacation package is an easy way to score an incredible deal. Plus, having your own wheels gives you the freedom to find your way to all those landmarks you're eager to see. Sitting 193 kilometers away from Canaan, Times Square is one attraction that should be on your can't-miss list. Fill up the tank and make a day trip of it.
Which airport is best for Canaan?
Bradley Intl. Airport (BDL) is 80 kilometers from downtown and is the starting point for many fun adventures. Alternatively, Albany Intl. Airport (ALB) is 48 kilometers away from central Canaan and Hartford, CT (HFD-Hartford - Brainard) is 97 kilometers away from central Canaan.
Where should I stay when visiting Canaan?
If you're searching for somewhere to lay your head, take a look at the Near Skiing! Hot Tub, Wood Stove, Pool Table, & Theater Room. Pet friendly!. It's the top pick for many visitors.

Photos of local treasures

Browse Canaan vacation photos for more inspiration

Photo by Robin/Loving Life
Photo by Robin/Loving Life