Canaan Vacations from $311

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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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $432, price is now $311 per person
$311
per person
Jun 19 - Jun 22
found 4 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (928 reviews)
Nice for families, has kitchen facilities for cooking. Door to room needs attention. Had to slam hard to close. Nice big bathroom. Thought we were getting 2 beds but had king bed and pull out couch. Wouldn’t always work for everyone. Could hear dog barking in nearby room. Price was right

Reviewed on May 17, 2026

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
Save 100% on your flight
Price was $650, price is now $457 per person
$457
per person
Jun 19 - Jun 22
found 4 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (894 reviews)
Family friendly resort with amenities the whole family can enjoy!

Reviewed on May 12, 2026

The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $1,061, price is now $753 per person
$753
per person
Jul 30 - Aug 4
found 22 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
9.2/10 Wonderful! (1,007 reviews)
Breakfast ok, coffee good, staff great

Reviewed on May 19, 2026

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $921, price is now $666 per person
$666
per person
Jul 23 - Jul 27
found 24 hours ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
9.4/10 Exceptional! (136 reviews)
Had a great stay. Beautiful location.

Reviewed on May 15, 2026

Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $766, price is now $578 per person
$578
per person
Jun 30 - Jul 3
found 15 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
6/10 (1 review)
The room was comfortable and well done. There was no heat in our room with no control for the air unit. There was also a drip coming from the exhaust fan in the bathroom. We were only there one night so I didn't call for support.

Reviewed on Apr 16, 2026

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Canaan Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from May 26 to May 27
$124 total
May 26 - May 27
Total with taxes and fees
9/10 Wonderful! (939 reviews)
"the Kitchen appeared to be fully equiped. The only cpmplaint I have was there were no avaiable plugs for mt CPAP machine nect to the bed> Easy fix is to offit the room with a multi plug on the night table.or lamp with plugs. Also there were no USB charging ports. Otherwise the facility was great"

Reviewed on May 19, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from May 25 to May 26
$124 total
May 25 - May 26
Total with taxes and fees
Berkshires Untold
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
$110 nightly
The price is $123 total per night from May 20 to May 21
$123 total
May 20 - May 21
Total with taxes and fees
8.8/10 Excellent! (2,361 reviews)
"Room was dated and needed a refresh but was clean"

Reviewed on May 17, 2026

Vacation Village in the Berkshires
See all 1,446 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
Closest Airport
Albany Intl. Airport (ALB)
Population
1,200
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
The Mac-Haydn Theatre, Shaker Museum and Library and Hudson Chatham Winery

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Frequently asked questions

How much does a Canaan vacation package cost?
You'll find cheap prices from $311 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.

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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.