Canaan Holidays

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Top hotels in Canaan

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Canaan NY
9.6/10 Exceptional! (15 reviews)
"Private, rustic cabin. Great communication from hosts. We hiked monument mountain while there. Highly recommend. Takes about 2.5 hours at a leisurely pace"

Reviewed on 13 Oct 2026

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Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
€90
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (2,794 reviews)
"Bathroom was filthy- The listing was for 12 miles from thunder mountain bike park and it ended up being 36 miles and hour away! Expensive for one night"

Reviewed on 25 Oct 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
€105
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (1,228 reviews)
"outside view,cleanness,large space"

Reviewed on 25 Oct 2026

Berkshire Mountain Lodge
See all 1,424 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.

Stay near popular Canaan attractions

Queechy Lake

Commune with nature and explore the great outdoors at Queechy Lake during your travels in Canaan. Discover the area's museums and shops.
See properties

Frequently asked questions

How much does a Canaan holiday package cost?
You'll find cheap prices 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 holiday to Canaan costs.
What are the cheapest months to go to Canaan?
The off-season is the best time to travel to Canaan if you're hoping to keep costs down. Another tip for getting cheap Canaan holiday packages? Try to avoid public holidays and any major events.
How many days is enough for Canaan?
With a well-organised travel plan, you can easily visit the main Canaan attractions in a few days. But if you'd like to venture off the beaten track or take day trips, think about booking your Canaan holiday for longer.
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 holiday package as soon as possible.
Is it cheaper to book a Canaan holiday as a package?
You can enjoy significant savings on your Canaan break by booking a tailored holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday 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.
How to plan a trip to Canaan?
  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Canaan.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to airfares and activities. Your hotel will likely be the biggest expense during your trip to Canaan.
  3. Determine how many days away: Start by compiling a list of the attractions you want to get to in Canaan. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Canaan holiday package.

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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.