Canaan Vacations from $447

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.
Coldbrook Bed and Breakfast

Coldbrook Bed and Breakfast

4 out of 5
Save 100% on your flight
Price was $649, price is now $447 per person
$447
per person
Oct 9 - Oct 12
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
10/10 Exceptional! (7 reviews)
Superbly designed B&B where comfort is found in every detail - from the beds to the fire pit with s'mores kits to the breakfast choices. Amazing experience - the modern, fresh and inviting design of this B&B is nestled in the woods with views of the mountains. We spent a long weekend here, exploring the local towns and trails by day, happy to come home to this lovely B&B every evening. We'll be back!

Reviewed on Aug 4, 2025

AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
Price was $1,007, price is now $720 per person
$720
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Hudson (HCC)
9/10 Wonderful! (409 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug 7, 2025

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $1,811, price is now $1,324 per person
$1,324
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Hudson (HCC)
9.4/10 Exceptional! (164 reviews)
Loved everything about it, especially large deck with view of waterfall. Interiors were beautiful and contemporary in a very convenient and comfortable way. No negatives.

Reviewed on Aug 18, 2025

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

3 out of 5
Save 100% on your flight
Price was $4,004, price is now $3,050 per person
$3,050
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Hudson (HCC)
No reviews
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
Save 100% on your flight
Price was $1,435, price is now $1,115 per person
$1,115
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Hudson (HCC)
9.2/10 Wonderful! (719 reviews)
Nice quiet place, very kind staff.

Reviewed on Aug 15, 2025

Don't see what you're looking for?
See all available trips from Columbus to Canaan
View all trips

Canaan Hotel Deals

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Sep 2 to Sep 3
$104 total
Sep 2 - Sep 3
Total includes taxes and fees
8.2/10 Very Good! (1,005 reviews)
Great stay
"The room was clean. The carpets need to be replaced. Water pressure not great. Breakfast was good but a little crowded. The staff was super friendly and helpful. Great location for the price."

Reviewed on Aug 15, 2025

Quality Inn
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
$227 nightly
The price is $254 total per night from Aug 26 to Aug 27
$254 total
Aug 26 - Aug 27
Total includes taxes and fees
8.8/10 Excellent! (1,005 reviews)
"Very clean, fantastic staff, comfortable bed, robes to use gping to the pool/jacuzzi, plus the large bottles of water in the room."

Reviewed on Aug 14, 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
$104 nightly
The price is $116 total per night from Sep 2 to Sep 3
$116 total
Sep 2 - Sep 3
Total includes taxes and fees
9/10 Wonderful! (694 reviews)
"Pleasant stay"

Reviewed on Aug 15, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 985 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.

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 $447 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.