Charlemont Vacations from $231

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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.

The Latest Charlemont vacation packages

Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $404, price is now $231 per person
$231
per person
Feb 26 - Mar 1
found 16 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Nice room with separate living room. We enjoyed the gym, pool and hot tub. We stayed on second floor and there is only one elevator, so you have to wait sometime. I wish there is stairs to walk down.

Reviewed on Jan 6, 2026

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
Price was $1,474, price is now $823 per person
$823
per person
Mar 13 - Mar 18
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was $823, price is now $476 per person
$476
per person
Feb 13 - Feb 20
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (2,013 reviews)
Really sharp, modern looking room. Excellent sound isolation from street noise. Bathroom isn't super private.

Reviewed on Jan 7, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $831, price is now $484 per person
$484
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Such a warm and cozy place with great amenities!

Reviewed on Dec 31, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,170, price is now $758 per person
$758
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Amazing week - family stay for Christmas in town - thank you very much! We’ll be back!…….

Reviewed on Dec 28, 2025

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Discover the most popular places to visit in Charlemont

Berkshire East Ski Resort

Hit the slopes in Charlemont with a visit to Berkshire East Ski Resort. Wander the forest or discover the area's waterfalls.

Berkshire East Ski Resort

Zoar Outdoor/Deerfield Valley Canopy Tours

Catch an event at Zoar Outdoor/Deerfield Valley Canopy Tours during your trip to Charlemont. Wander the forest or discover the area's waterfalls.

Zoar Outdoor/Deerfield Valley Canopy Tours

Bissell Covered Bridge

Learn about the local history of Charlemont with a stop at Bissell Covered Bridge. Wander the forest or discover the area's waterfalls.

Bissell Covered Bridge

Charlemont Hotel Deals

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
$126 nightly
The price is $141 total per night from Jan 11 to Jan 12
$141 total
Jan 11 - Jan 12
Total with taxes and fees
8.6/10 Excellent! (2,200 reviews)
Clean rooms, chimney did not work

Reviewed on Jan 4, 2026

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$125 nightly
The price is $140 total per night from Feb 2 to Feb 3
$140 total
Feb 2 - Feb 3
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
friendly accommodating staff

Reviewed on Jan 1, 2026

Hotel Downstreet, an Ascend Collection Hotel
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$98 nightly
The price is $109 total per night from Jan 23 to Jan 24
$109 total
Jan 23 - Jan 24
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN

Reviewed on Jan 4, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,504 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.

Find the Best Charlemont Vacation Packages

Charlemont Essential Information

Language
English
Currency
U.S dollars
Population
1,400
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Double Edge Theatre, Bissell Covered Bridge and Ashfield Lake

Charlemont Ski Vacation Packages

Do things your way with one of our Charlemont ski vacation packages. Whether you're into an adrenaline-filled adventure, tranquility at altitude or both, your ultimate escape starts with Expedia. Make your way to Charlemont between December and April and you'll discover around 38 ski runs in operation at this well-known winter destination in United States of America. Wander around the ski village and stock up on any equipment you need for downhill skiing. If you're new to the slopes, there's at least one beginners' area where you can learn the basics. When you're ready to leave the slopes, make your way to the day spa here. It's an excellent way to recharge after hours of downhill action. The kids will enjoy themselves on your family ski vacation in Charlemont, with memorable activities such as night skiing, snowboarding and tobogganing available too.

How To Get Around

Many ski travelers who reserve one of our Charlemont vacation packages jet into Albany International Airport. From there, it's two hours before you're zigzagging down the slopes of Charlemont's favorite runs. From the middle of Charlemont, the ski runs are around under 5 minutes away by car and parking is free. In winter, it's best to carry tire chains. You can pick from five-day, season-pass, multi-resort pass and half-day tickets. When it's time to plan your ski vacation, scroll through Expedia's Charlemont ski package deals. Combine your flights, hotel and car rental and enjoy big savings on your snowy adventure.

Charlemont Things to do

Swap ski stories (and a few drinks) with friends at Crazy Horse Bar and Grill. It's the place to get your après-ski on when you're done with the slopes. Festivals, live DJs or bands and an exciting nightlife add to the great vibe of Charlemont. Whitewater activities, mountain biking, alpine coasters and zip-lining will keep you on the go if you'd prefer to travel in summer. Whether you're planning a Charlemont ski vacation or a summery escape, add some activities to your vacation package for the ultimate stay.

Charlemont Resort Ski Info

Average yearly snowfall
9.2 ft
Elevation of lowest ski lift
520 ft
Cost of 1-day lift pass
Under $100
Easy runs
11
Moderate runs
14
Advanced runs
13
Longest run
2.5 mi

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Frequently asked questions

How much does a Charlemont vacation package cost?
You'll find cheap prices from $231 on Expedia for your Charlemont getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Charlemont costs.
What are the cheapest months to go to Charlemont?
If you're hoping to score a cheap Charlemont vacation package, consider traveling in June, November and December. You'll generally find better prices on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Charlemont?
Usually, a handful of days is enough to tick off the major attractions during your Charlemont vacation. But if you'd like to have more time to unwind or go on day tours, consider extending your itinerary.
Is it worth booking a vacation package to Charlemont?
Charlemont is a good vacation destination with attractions like Berkshire East Ski Resort among the many things to keep you busy. Whether you're traveling with the family or planning a trip with friends, a Charlemont vacation promises fun for everyone.
How to find the best Charlemont package deals?
Begin your search for a Charlemont package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Charlemont package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Charlemont escape underway.
Is it cheaper to book a Charlemont vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still get the freedom to create a customized Charlemont vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Charlemont?
If you're considering an impromptu Charlemont trip, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Charlemont vacation packages?
Your Charlemont break is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.