Canaan Vacations from $621

Book a Hotel + Flight or Car together to unlock savings

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.
The Hidden Inn

The Hidden Inn

4 out of 5
Price was $740, price is now $621 per person
$621
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hudson (HCC)
8.8/10 Excellent! (51 reviews)
We arrived at night in time for a cocktail and an appetizer.Everything was great .Room was immaculate and quiet. Would definitely stay again if in area .

Reviewed on Oct 10, 2025

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

3 out of 5
Save 100% on your flight
Price was $2,877, price is now $2,056 per person
$2,056
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
10/10 Exceptional! (1 review)
We encountered issues with the kitchen lightings and dish washer. Other than that, the house is beautiful and spacious.

Reviewed on Sep 27, 2025

The Haüs Windham

The Haüs Windham

2 out of 5
Save 100% on your flight
Price was $2,828, price is now $2,142 per person
$2,142
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
8.6/10 Excellent! (15 reviews)
Hot tub could have been cleaner but all in all. Beautiful and amazing views! Great service with the front desk calls and extra towels provided no problem!

Reviewed on Sep 15, 2025

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

Ski Hike Lodge 5BR w Fire Pit Cozy Spaces

2 out of 5
Save 100% on your flight
Price was $6,020, price is now $4,612 per person
$4,612
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
No reviews
Perfect Family Vacation Home in the Mountains

Perfect Family Vacation Home in the Mountains

2 out of 5
Price was $1,582, price is now $1,375 per person
$1,375
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hudson (HCC)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Canaan
View all trips

Canaan Hotel Deals

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
$181 nightly
The price is $203 total per night from Nov 23 to Nov 24
$203 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
In a very nice annex suite.

Reviewed on Oct 18, 2025

The Red Lion Inn
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
$142 nightly
The price is $158 total per night from Nov 2 to Nov 3
$158 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (757 reviews)
Awesome visit to the Berkshires!
The room was spotless and a perfect fit for our needs.

Reviewed on Oct 15, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 Nov 13 to Nov 14
$114 total
Nov 13 - Nov 14
Total with taxes and fees
8.8/10 Excellent! (678 reviews)
This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well.

Reviewed on Oct 18, 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
See all 992 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 from $621 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.