Charlemont Vacation Packages 2026 from $495

Charlemont flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Battery Wharf Hotel, Boston Waterfront

North End

$495

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a sauna on site, and laundry facilities and concierge services are also offered.

Boston Harbor Hotel

North End

Save 100% on your flight

$855

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$2,076

per person

Dec 22 - Dec 28

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Raffles Boston

Back Bay

Save 100% on your flight

$1,250

per person

Dec 23 - Dec 28

found 24 hours ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

$2,387

per person

Dec 5 - Dec 11

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the sauna and perks like free WiFi.

Top Charlemont hotels deals

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Hawley MA

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$143 total

Nov 1 - Nov 2

Total with taxes and fees

This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Parking included

Hotel UMass

1 Campus Center Way Amherst MA

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This hotel features 5 coffee shops/cafes and a bar/lounge. Enjoy a meal from the restaurant and perks like free continental breakfast and free WiFi. Self parking, a snack bar/deli, and a lobby fireplace are also offered.

Breakfast included

Free WiFi

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$115 nightly

$128 total

Nov 15 - Nov 16

Total with taxes and fees

This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.

Pool

Hot Tub

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$112 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Hotel On North

297 North Street Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$166 total

Nov 1 - Nov 2

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking and luggage storage are also offered on site.

Pet friendly

Parking included

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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 Charlemont attractions

A wooden boardwalk through a forest with snow patches and bare trees.

Hawley Bog Preserve

Explore the great outdoors at Hawley Bog Preserve, a lovely green space in Hawley. Wander the forest or discover the area's waterfalls.

See properties

Frequently asked questions

How much are vacation packages to Charlemont?

With vacation packages being sold from as little as $495, it's not necessary to wipe out your bank balance for your getaway to Charlemont. Travelocity is here to help. Bundle your flights, hotels and tours into a package and receive some fantastic discounts. The more you book, the greater the savings.

Where can I get the best vacation package deals for Charlemont?

It's hard to look past Travelocity when it comes to putting together your Charlemont package deal. There are at least 400 airlines and 1,000,000 properties worldwide to select from. Secure your trip now and get ready to tick another amazing place off your to-do list.

Why should I purchase my Charlemont vacation bundle with Travelocity?

We take the stress out of travel planning. Whether you're looking for an amazing new place to explore or want to ensure you get the best deal around, we've got your back. Our 24/7 customer care, excellent service and Price Match Guarantee mean you can book with confidence.

Can I save money on my Charlemont car rental if I combine it with my hotel or flight?

Absolutely — combine your hotel, car and flight into a Charlemont vacation package and you'll save plenty. With so many things to do in the Charlemont area, that set of wheels will make exploring a joy. Once you've buckled up, put the stereo on and head toward Fenway Park, an unmissable sight about 90 mi from Charlemont.

Which airport is best for Charlemont?

One top option is Bradley Intl. Airport (BDL). From here, you'll need to travel north for roughly 50 mi to reach the heart of Charlemont. Another convenient choice is Albany Intl. Airport (ALB), which is 50 mi away from central Charlemont.

What is there to do in Charlemont?

You'll feel a certain kind of magic as you roam the streets of Charlemont. Charlemont Federated Church and Hail to the Sunrise Statue are just a couple of famous attractions that make this city such a sought-after destination, so put them on your must-see list.

Where should I stay when visiting Charlemont?

The Hawley Home w/ Deck: 4 Mi to Berkshire East Resort is the number one choice of many travelers. Book as soon as possible to avoid missing out.