Deals on vacations and trips to Canaan

Save when you book Canaan package deals

Choose two or more items and save on your trip:

Canaan flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Hidden Inn

The Hidden Inn

4 out of 5
Price was $1,414, price is now $992 per person
$992
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip flight included
New York (JFK) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $2,033, price is now $1,310 per person
$1,310
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip flight included
New York (JFK) to Albany (ALB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Price was $1,488, price is now $1,034 per person
$1,034
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip flight included
New York (JFK) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $1,685, price is now $1,178 per person
$1,178
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip flight included
New York (JFK) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.
Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Roundout
Save 100% on your flight
Price was $5,957, price is now $4,177 per person
$4,177
per person
Dec 22 - Dec 27
found 20 hours ago
Roundtrip flight included
New York (JFK) to Albany (ALB)
This guesthouse features an area shuttle, free self parking, and free WiFi in public areas. Enjoy the free continental breakfast each morning. A business center, a terrace, and a garden are also on offer.

Top Canaan hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $125 total per night
$125 total
Nov 12 - Nov 13
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $126 total per night
$126 total
Nov 9 - Nov 10
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.
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
$98 nightly
The price is $109 total per night
$109 total
Dec 5 - Dec 6
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.
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $115 total per night
$115 total
Nov 16 - Nov 17
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.
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
Free Cancellation
$110 nightly
The price is $122 total per night
$122 total
Nov 30 - Dec 1
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a picnic area, and laundry facilities are also on offer.
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
$186 nightly
The price is $208 total per night
$208 total
Nov 12 - Nov 13
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.
Don't see what you're looking for?
See all available properties in Canaan
View all properties
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 $992. 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

Browse Canaan vacation photos for more inspiration

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

Explore More Ways to Travel with Travelocity