Canaan Vacations from $1,019

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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.

The Latest Canaan vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $1,299, price is now $1,019 per person
$1,019
per person
Dec 21 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Hudson (HCC)
9.4/10 Exceptional! (888 reviews)
Great staff

Reviewed on Nov 4, 2026

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Price was $6,064, price is now $4,699 per person
$4,699
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
No reviews

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Price was $6,077, price is now $4,711 per person
$4,711
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
No reviews

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,530, price is now $1,276 per person
$1,276
per person
Dec 21 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Hudson (HCC)
8.8/10 Excellent! (133 reviews)
Room super clean and beautiful property!

Reviewed on Nov 2, 2026

Windham NY Escape

Windham NY Escape

3 out of 5
Price was $1,908, price is now $1,687 per person
$1,687
per person
Dec 21 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Hudson (HCC)
10/10 Exceptional! (2 reviews)

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Stay near popular Canaan attractions

C H Pease Museum

This Victorian-era natural history collection showcases meticulously preserved local wildlife from the 1800s. Examine rare bird specimens and vintage taxidermy in North Canaan's historic Douglas Library.
See properties

Canaan Hotel Deals

Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
$76 nightly
The price is $85 total per night from Nov 29 to Nov 30
$85 total
Nov 29 - Nov 30
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"Office staff wonderful! Room clean but older carpet and bathroom looked dingy."

Reviewed on Nov 3, 2026

Quality Inn Great Barrington
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

3.5 out of 5
190 Meadow Street South Lee MA
Fully refundable
$135 nightly
The price is $150 total per night from Nov 8 to Nov 9
$150 total
Nov 8 - Nov 9
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"Condo was super clean, spacious and comfortable. Really nice having a full kitchen, too. Staff was accommodating when we decided to add an extra night to our vacation. Great place to stay if you’re going to a concert at Tanglewood."

Reviewed on Nov 3, 2026

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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
$195 nightly
The price is $218 total per night from Nov 12 to Nov 13
$218 total
Nov 12 - Nov 13
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
"Enjoyable stay. We will come back."

Reviewed on Nov 4, 2026

The Red Lion Inn
See all 1,021 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

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Frequently asked questions

How much does a Canaan vacation package cost?
You'll find cheap prices from $1,019 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.

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