Canaan Vacations from $665

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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.
Eastwind Windham

Eastwind Windham

2 out of 5
Price was $820, price is now $665 per person
$665
per person
Nov 20 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hudson (HCC)
9.2/10 Wonderful! (60 reviews)
Friendly staff, accommodating and clean Some of it under construction

Reviewed on May 23, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Price was $911, price is now $689 per person
$689
per person
Nov 20 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hudson (HCC)
9/10 Wonderful! (417 reviews)
We enjoyed an overnight stay at this Air Stream when we visited Kaaterskill Falls for our anniversary. Clean & spacious bathroom, nice to be able to take a hot shower after a full day hike. Kitchenette well equipped with mini fridge, microwave, electric kettle & dinnerware & utensils. Private picnic table & fire pit outside for campfire & cooking but you have to buy the firewood which wasn’t included in the resort fee. Had dinner at the clubhouse kitchen, burger was delicious. In the morning hiked the trail around the campground, very peaceful & quiet. Overall we had a memorable stay.

Reviewed on Oct 4, 2025

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $1,666, price is now $1,270 per person
$1,270
per person
Nov 20 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hudson (HCC)
9.6/10 Exceptional! (180 reviews)
I loved the Tannery Brook suites is the way go.

Reviewed on Oct 3, 2025

Modern Catskills Escape w/ Open Living, Steam Shower, Fireplace & Hot Tub w/ Mountain Views, Minutes From Woodstock & Trails Suncliff Vista

Modern Catskills Escape w/ Open Living, Steam Shower, Fireplace & Hot Tub w/ Mountain Views, Minutes From Woodstock & Trails Suncliff Vista

3 out of 5
Price was $1,507, price is now $1,182 per person
$1,182
per person
Nov 20 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hudson (HCC)
No reviews
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was $813, price is now $671 per person
$671
per person
Nov 20 - Nov 24
found 10 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hudson (HCC)
9.2/10 Wonderful! (278 reviews)
Wonderful resort, clean , great facilities friendly staff

Reviewed on Oct 7, 2025

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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 refundableReserve now, pay when you stay
$129 nightly
The price is $144 total per night from Nov 2 to Nov 3
$144 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (749 reviews)
"This is a fun family resort... a great vacation place .. in a great location.. something for everyone. Perfect family reunion place.. All Ages happy.."

Reviewed on Oct 6, 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
$180 nightly
The price is $202 total per night from Nov 6 to Nov 7
$202 total
Nov 6 - Nov 7
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
"."

Reviewed on Oct 6, 2025

The Red Lion Inn
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Nov 2 to Nov 3
$94 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"Very basic and affordable"

Reviewed on Oct 4, 2025

Quality Inn
See all 989 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.

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 $665 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

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.