Deals on vacations and trips to Canaan

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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
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
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
$76 nightly
The price is $85 total per night
$85 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
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
$93 nightly
The price is $104 total per night
$104 total
Dec 25 - Dec 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night
$120 total
Jan 21 - Jan 22, 2026
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
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
$178 nightly
The price is $199 total per night
$199 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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $127 total per night
$127 total
Dec 24 - Dec 25
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
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

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

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 120 mi 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 50 mi from downtown and is the starting point for many fun adventures. Alternatively, Albany Intl. Airport (ALB) is 30 mi away from central Canaan and Hartford, CT (HFD-Hartford - Brainard) is 60 mi 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

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

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