Canaan Holidays

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Top hotels in Canaan

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is €207 per night from 22 Jul to 23 Jul
€207
22 Jul - 23 Jul
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Steven’s House (a Red Lion Annex across the street) is very “tired”. Exterior has severe wear with peeling paint and unkempt yard. Interior is much the same with wallpaper peeling in bathroom, a broken ice machine in the common area. The cleanliness is below expected for the price paid ( same as ..."

Reviewed on 13 Jul 2026

The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
The price is €116 per night from 6 Aug to 7 Aug
€116
6 Aug - 7 Aug
includes taxes & fees
8.6/10 Excellent! (1,020 reviews)
"Comfortable rooms within walking distance to Great Barrington."

Reviewed on 13 Jul 2026

Quality Inn Great Barrington
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
The price is €174 per night from 29 Jul to 30 Jul
€174
29 Jul - 30 Jul
includes taxes & fees
9.2/10 Wonderful! (936 reviews)
"We enjoyed the activities. The room was also spacious."

Reviewed on 13 Jul 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 1,029 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

Edith Scoville Memorial Sanctuary

Traverse lush forests to Lion's Head Peak at this tranquil Connecticut sanctuary. The challenging trail rewards hikers with panoramic views of rolling hills and vibrant fall foliage.
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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.

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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.