Canaan Vacations from $549

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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.
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $671, price is now $549 per person
$549
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
17.6/10 Exceptional! (600 reviews)
Great location Everything updated Pleasant greeting in lobby

Reviewed on Nov 25, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $819, price is now $605 per person
$605
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
14.8/10 Exceptional! (567 reviews)
We feel that the resort fee to access the pool and hot tub as well as the other services covered are over priced. We stay at resorts and hotels all over the US and you are the ONlY place that charges for this.

Reviewed on Nov 21, 2025

The Manchester View

The Manchester View

2.5 out of 5
Price was $760, price is now $626 per person
$626
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
18.8/10 Exceptional! (772 reviews)
Staff was very helpful. The room was cosy with everything I needed. Old time hotel with good value. I’d stay there again.

Reviewed on Oct 26, 2025

South Shire

South Shire

4 out of 5
Price was $704, price is now $594 per person
$594
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
18/10 Exceptional! (116 reviews)
Very cool rooms. Al different and many with fireplaces. Friendly staff

Reviewed on Oct 31, 2025

Weathervane Motel

Weathervane Motel

2 out of 5
Price was $783, price is now $662 per person
$662
per person
Dec 31 - Jan 4
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
13.6/10 Exceptional! (724 reviews)
Everything was great and we will stay there again 😁

Reviewed on Nov 16, 2025

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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
$94 nightly
The price is $105 total per night from Nov 29 to Nov 30
$105 total
Nov 29 - Nov 30
Total with taxes and fees
8.6/10 Excellent! (2,146 reviews)
Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. ...

Reviewed on Nov 22, 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
$120 nightly
The price is $135 total per night from Dec 7 to Dec 8
$135 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (763 reviews)
The room was very clean, appreciated the friendly and helpful staff. Well stocked kitchen, super close to grocery stores and restaurants.

Reviewed on Nov 21, 2025

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$89 nightly
The price is $100 total per night from Nov 29 to Nov 30
$100 total
Nov 29 - Nov 30
Total with taxes and fees
7.8/10 Good! (965 reviews)
Great checking. Great staff, great room.

Reviewed on Nov 22, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,406 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 $549 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.