Canaan Vacation Packages

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Your Canaan Vacation

Say bye-bye to planning hassles and hello to a Canaan vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with Canann Village Historic District, which is good for dining, culture and shopping. If taking in sights is on the agenda during your trip to Canaan, check out top attractions like Mount Riga State Park, Mount Frissell and Land of Nod Vineyard and Winery. Check out Expedia's wide range of travel options and book your ideal vacation to Canaan today.

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Canaan Hotel Deals

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 refundable
The price is CA $195 per night from Jul 30 to Jul 31
CA $195
CA $237 total
Jul 30 - Jul 31
includes taxes & fees
9/10 Wonderful! (680 reviews)
Enjoyed our stay.
"Our family stay was very nice. We took advantage of the large outdoor pool and the mini golf on site. The property is in a very beautiful woodsy minimally developed area. The unit was fine but not great. The cabinets are generally old looking and water-moisture damaged. All was workable but 5 star ..."

Reviewed on Jul. 23, 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 CA $250 per night from Aug 25 to Aug 26
CA $250
CA $341 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Miranda at the front desk was beyond accommodating. My mom and I enjoyed our stay in this historic hotel!"

Reviewed on Jul. 21, 2025

The Red Lion Inn
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 CA $138 per night from Aug 7 to Aug 8
CA $138
CA $154 total
Aug 7 - Aug 8
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
Budget friendly Tanglewood accommodation
"Hotel was great for a night at Tanglewood. Location key. Nice that we could walk around Great Barrington in search of breakfast. Easy to find. Clean."

Reviewed on Jul. 22, 2025

Quality Inn
See all 979 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Canaan vacation package cost?
You'll find cheap prices on Expedia for your Canaan escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Canaan costs.
What are the cheapest months to go to Canaan?
If you're hoping to snag a cheap Canaan vacation package, consider travelling in January, February and March. You'll generally find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Canaan?
We'd suggest booking a Canaan vacation for at least 2 days. This will allow you plenty of time to tick off popular sights such as Campbell Falls State Park and Land of Nod Vineyard and Winery, and explore neighbourhoods like North Canaan and East Canaan. You could even make time for one or two day trips beyond Canaan.
How to find the best Canaan package deals?
Begin your search for a Canaan package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Canaan package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Canaan getaway off to a flying start.
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. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
How to plan a trip to Canaan?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Canaan.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will likely be the biggest expense during your trip to Canaan.
  3. Decide how many days away: Start by making a list of all the attractions and activities 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 flights, hotels, car rental 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.