Canaan Vacations from $447

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Your Canaan Vacation

With a Canaan vacation package, say goodbye to endless planning and hello to stress-free adventure. Every detail of your escape has been taken care of before you depart, so you can make the most of your time discovering this lively city. When the time comes to head out and explore, be sure to include Mount Lebanon Shaker Village and New Lebanon Library on the itinerary for your trip to Canaan. Expedia has what you need to escape the everyday. Tailor your vacation to Canaan to match your travel style, whatever that may be.

The Latest Canaan vacation packages

Price found within the past 48 hours. Click for updated prices.
Coldbrook Bed and Breakfast
Woodstock Way Hotel
The Equinox Golf Resort & Spa
Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly
The Wiltwyck
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Canaan Hotel Deals

Cozy cabin in tranquil Canaan NY with WiFi, AC

Cozy cabin in tranquil Canaan NY with WiFi, AC

Canaan
Cozy cabin in tranquil Canaan NY with WiFi, AC
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $145 total per night from Aug 27 to Aug 28
$145 total
Aug 27 - Aug 28
Total includes taxes and fees
8.6/10 Excellent! (1,950 reviews)
Love Vacation Village!
"Love everything about this place. If you want a true home away from home this is the place. The only miss is streaming abilities for at night, but an extra hdmi to type C cable,and we were all set!"

Reviewed on Aug 16, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $96 total per night from Sep 7 to Sep 8
$96 total
Sep 7 - Sep 8
Total includes taxes and fees
8.8/10 Excellent! (581 reviews)
"Enjoyed the room, towels and kitchen. I can recommend."

Reviewed on Aug 18, 2025

Berkshire Mountain Lodge
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.

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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 influence how much your vacation to Canaan costs.
What are the cheapest months to go to Canaan?
You can typically find reduced prices and better availability in June, September and October. Browse our cheap Canaan vacation packages and you could land some great off-season discounts.
How many days is enough for Canaan?
The ideal length for your Canaan vacation depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to hit all the top attractions and discover some hidden gems along the way.
How to find the best Canaan package deals?
Use Expedia's filters to help you find some terrific Canaan package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Canaan package deals in the off-season. Play around with your travel dates and you may score even bigger 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?
You can enjoy significant savings on your Canaan break by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Canaan?
Secure amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Canaan escape.
Does Expedia offer Book Now, Pay Later Canaan vacation packages?
Your Canaan trip is meant to be an escape from your busy life, not a source of money-related stress. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no 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.