Canaan Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Canaan

Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is 3.083.124 ₫ per night from 13 Jul to 14 Jul
3.083.124 ₫
3.443.850 ₫ total
13 Jul - 14 Jul
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"The gentleman working at the front desk was extremely helpful when were in a pinch and needed assistance late at night! The second-level room was comfortable, clean, and quiet, and the location is amazing, just a short walk to all the restaurants, cafes and shops that downtown Great Barrington has ..."

Reviewed on 26 Jun 2025

Quality Inn
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
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is 4.203.904 ₫ per night from 1 Jul to 2 Jul
4.203.904 ₫
5.060.047 ₫ total
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (660 reviews)
Good for a girls trip!
"We loved the comfortable beds and ensuite bathrooms. The kitchen was well-equipped and common room was comfortable too. We didn't use any of the other amenities, but there were quite a few options that looked appealing. Convenient to Lenox which was our primary destination for dining and ..."

Reviewed on 21 Jun 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is 5.662.615 ₫ per night from 7 Jul to 8 Jul
5.662.615 ₫
7.491.091 ₫ total
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Lovely inn, friendly staff in every area. And a fabulous porch. This is the rare old inn that feels modern, too, and it overflows with charm."

Reviewed on 26 Jun 2025

The Red Lion Inn
See all 965 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 determine how much your holiday to Canaan costs.
What are the cheapest months to go to Canaan?
January, February and March are the best times to search for cheap Canaan holiday packages. Travelling in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Canaan?
The ideal length of your Canaan holiday depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to visit all the top sights and discover some hidden gems along the way.
How to find the best Canaan package deals?
Use Expedia's filter tool to help you find some of the best Canaan package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Canaan package deals in the off-peak season. Play around with your travel dates and you may land even better 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?
An Expedia holiday package could land you great savings when compared to arranging flights and accommodation separately. Better still, you can customise your Canaan trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Canaan?
Score incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Canaan trip.
How to plan a trip to Canaan?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Canaan.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and activities. Your hotel will likely be the largest expense during your trip to Canaan.
  3. Decide how long to go away for: Now that you know more about Canaan, you can figure out the ideal length of your holiday. Put together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Canaan holiday package that brings all your bookings together.