Charlemont Vacation Packages

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Your Charlemont Vacation

The fascinating city of Charlemont is calling your name. Discover its hot spots and hidden treasures with a Charlemont vacation package that's tailored to you. Berkshire East Ski Resort, Charlemont Federated Church and Hawley Bog Preserve are just a few of the many sights worth visiting during your trip to Charlemont. Browse Expedia's extensive range of travel options and start organizing your dream vacation to Charlemont now.

Top Charlemont Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Excellent hotel with friendly staff, clean and comfortable rooms with a Starbucks! We love the cookies at check in. always a winner. It is in a weird location but for our one night it was great.

Reviewed on Jul. 14, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Location is perfect. A lots of places to see within walking distance and good restaurants nearby too. The service is great. Friendly and professional staff. The room is clear and spacious. The gym is very big with all the equipments and have personal training rooms too. We stayed 5 nights and were very lucky to get room on 16th floor with a balcony!

Reviewed on Jul. 14, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Free breakfast and airport shuttles were a win! Very easy to navigate the shuttle schedule.

Reviewed on Jul. 14, 2025

Ready to book your vacation to Charlemont?

 

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Charlemont Hotel Deals

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Hawley
9.6/10 Exceptional! (99 reviews)
Peaceful Get-away
"We really enjoyed our stay. Watching all the wildlife come and go around the pond was a highlight. Thanks!"

Reviewed on Jun. 23, 2025

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Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Bear Creek Cabin
Bear Creek Cabin
Charlemont
The price is CA $548 per night from Jul 20 to Jul 21
CA $548
CA $820 total
Jul 20 - Jul 21
includes taxes & fees
9.8/10 Exceptional! (31 reviews)
Marvelous weekend
"The cabin is lovely. Everything you need is there and more. Great location. Went to Crabapple Rafting. Spent a day in Shelburne falls shopping and lunch. Kids really enjoyed our 4 days there."

Reviewed on Jul. 2, 2025

Bear Creek Cabin
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 CA $110 per night from Jul 15 to Jul 16
CA $110
CA $137 total
Jul 15 - Jul 16
includes taxes & fees
8.6/10 Excellent! (1,867 reviews)
"Wonderful property in an idyllic setting! Everything you need for a quality vacation with friends or family. One of the most relaxing getaways I've ever had."

Reviewed on Jul. 11, 2025

Vacation Village in the Berkshires
See all 1,457 properties in Charlemont
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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Charlemont vacation package cost?
Offering great value package deals from CA $631 on Expedia, you'll be surprised at how little a vacation to Charlemont costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Charlemont?
Plan your trip for the off-peak season and you're likely to get cheap Charlemont vacation packages. Bear in mind that school vacation periods and major events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Charlemont?
With a well-organized schedule, you can easily hit the most popular Charlemont sights in a handful of days. But if you want to venture off the beaten track or take day trips, consider booking your Charlemont vacation for longer.
Is it worth booking a vacation package to Charlemont?
Charlemont is a good vacation destination with attractions like Charlemont Federated Church among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Charlemont vacation promises fun for everyone.
How to find the best Charlemont package deals?
Use Expedia's handy filters to find some of the best Charlemont package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Charlemont package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Charlemont vacation as a package?
You can enjoy significant savings on your Charlemont getaway by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Charlemont?
Enjoy amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Charlemont break.
How to plan a trip to Charlemont?

  1. Pick your travel dates: The things you want to do in Charlemont and your favourite season can help you decide when to go.
  2. Plan your budget wisely: On top of the price of your accommodations, you'll need to consider other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that could arise during your trip to Charlemont.
  3. Decide how many days away: Start by listing all the activities and attractions you want to get to in Charlemont. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Charlemont vacation package.

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