Canaan Trips (flight + hotel)

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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 P5,267 per night from Aug 27 to Aug 28
P5,267
P6,513 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (1,923 reviews)
"The unit has everything you need and is very clean. It would benefit from a step stool in the kitchen area because you can't reach the dishes without standing on a chair. Also it says you MUST use a convention pan to use the cooktop but there isn't one. Parking is difficult -- the spaces area too ..."

Reviewed on Aug 3, 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
8.8/10 Excellent! (542 reviews)
"Overall great. Located to many of the attractions in area. Grocery store across the street. Only downfall was the room was noisy in the night from being on ground floor. Other than that can not beat the quality for the price!"

Reviewed on Aug 4, 2025

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Berkshire Mountain Lodge
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 P4,079 per night from Aug 24 to Aug 25
P4,079
P4,556 total
Aug 24 - Aug 25
includes taxes & fees
5.2/10 (761 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on Aug 2, 2025

FairBridge Inn Express
See all 1,420 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 vacation 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 vacation 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 vacation packages? Try to avoid public holidays and any major events.
How many days is enough for Canaan?
With a well-organized 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 vacation 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 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.
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 vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.