Canaan Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Robin/Loving Life

Top hotels in Canaan

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
The price is 2.277.056 ₫ per night from 25 Aug to 26 Aug
2.277.056 ₫
2.831.028 ₫ total
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (1,918 reviews)
Great resort condo for price of a hotel room!
"Clean, comfortable one bedroom condo with full size fridge, microwave, 2 burner hotplate and plenty of dishes, glasses, silverware, and pans. Beautiful location with many resort features for the whole family. Staff is wonderful and quick to respond if you need help with anything in the condo."

Reviewed on 1 Aug 2025

Vacation Village in the Berkshires
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is 1.862.678 ₫ per night from 17 Aug to 18 Aug
1.862.678 ₫
2.080.645 ₫ total
17 Aug - 18 Aug
includes taxes & fees
5.2/10 (756 reviews)
"Well the little fridge they had in the room hummed loudly all the time the freezer needed to be defrosted I bought a couple of frozen dinners and couldn't get both of them in the freezer. One of the draws on the side tables when I pulled open the drawer one side of the handle came loose I was able ..."

Reviewed on 28 Jul 2025

FairBridge Inn Express
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is 11.111.462 ₫ per night from 8 Aug to 9 Aug
11.111.462 ₫
12.411.504 ₫ total
8 Aug - 9 Aug
includes taxes & fees
9/10 Wonderful! (654 reviews)
"Very nice hotel, convenient location to Tanglewood and other attractions. Quiet and comfortable beds."

Reviewed on 30 Jul 2025

Berkshires Untold
See all 1,427 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.

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.