Canaan Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Canaan Vacation

Say bye-bye to planning hassles and hello to a Canaan vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. If taking in sights is on the agenda during your trip to Canaan, check out top attractions like Mount Riga State Park, Mount Frissell and Land of Nod Vineyard and Winery. Check out Expedia's wide range of travel options and book your ideal vacation to Canaan today.

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
Fully refundable
$152 nightly
The price is $169 total per night from Dec 8 to Dec 9
$169 total
Dec 8 - Dec 9
Total with taxes and fees
9/10 Wonderful! (795 reviews)
I loved the room we stayed in, it really gave a townhouse feel. It made you feel like you were staying in a real home. I just wished that the resort's activity center had more to offer in their grab and go eating area. They do not serve breakfast and their menu is very limited for lunch/dinner hours. ...

Reviewed on Dec 5, 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
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $212 total per night from Dec 18 to Dec 19
$212 total
Dec 18 - Dec 19
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Great location, nice rooms, and excellent price n house dining. Next time I go I’ll try to get top floor room, sounded like a basketball team were in room above my 2nd floor room

Reviewed on Dec 1, 2025

The Red Lion 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
Fully refundable
$102 nightly
The price is $114 total per night from Dec 15 to Dec 16
$114 total
Dec 15 - Dec 16
Total with taxes and fees
8.8/10 Excellent! (703 reviews)
We stay here every year and it never disappoints

Reviewed on Dec 5, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
See all 1,001 properties in Canaan
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 the Best Canaan Vacation Packages

Canaan Essential Information

Language
English
Currency
U.S dollars
Population
1,200
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Mount Frissell, Campbell Falls State Park and Haystack Mountain State Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Canaan vacation package cost?
You'll find cheap prices on Expedia for your Canaan escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Canaan costs.
What are the cheapest months to go to Canaan?
You're likely to find reduced prices and greater availability in December, January and February. Explore our cheap Canaan vacation packages and you could get some great off-season deals.
How many days is enough for Canaan?
The ideal length of your Canaan vacation depends on what you'd like to do. Usually, a few days to a week will give you plenty of time to check out all the leading attractions and discover some hidden treasures along the way.
How to find the best Canaan package deals?
Use Expedia's filter tool to help you find some of the best Canaan package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Canaan package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Canaan vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations separately. Better still, you can customize your Canaan trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Canaan?
Score incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Canaan trip.
Does Expedia offer Book Now, Pay Later Canaan vacation packages?
Your Canaan getaway is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.