Western Massachusetts Trips (flight + hotel)

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Where to stay in Western Massachusetts

Find the best Western Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Western Massachusetts
Springfield featuring heritage architecture

Metro Center

1 out of top 10 points of interest in this area

If you're spending some time in Metro Center, Paramount Theater and MassMutual Center are top sights worth seeing.

Find hotels in Metro Center

Top hotels in Western Massachusetts

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 P6,183 per night from Aug 27 to Aug 28
P6,183
P7,532 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (1,945 reviews)
"Very nice"

Reviewed on Aug 15, 2025

Vacation Village in the Berkshires
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
The price is P9,075 per night from Sep 1 to Sep 2
P9,075
P11,591 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,391 reviews)
"Nice"

Reviewed on Aug 14, 2025

MGM Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (571 reviews)
"Shower/tub side in accessible room was extremely high fyi."

Reviewed on Aug 17, 2025

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Berkshire Mountain Lodge
See all 1,483 properties in Western Massachusetts
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.

Popular places to visit

Tanglewood Music Center

Tanglewood Music Center

You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.

Tanglewood Music Center

Frequently asked questions

How much does a Western Massachusetts vacation package cost?
We make it simple for everyone to travel, with Western Massachusetts vacation packages starting from just . You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a couple of experiences and tours to your itinerary?
How do I get a cheap travel package to Western Massachusetts?
One of the simplest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got them all. Pick the combination that best suits you and see your savings grow. We know a travel package is never a one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 properties around the globe, which lets you customize your Western Massachusetts getaway.
Where should I stay in Western Massachusetts?
If you've always dreamed of exploring Naismith Memorial Basketball Hall of Fame and Volleyball Hall of Fame, the city of Springfield is calling your name.
What are the top hotels in Western Massachusetts?
Take a look at Hampton Inn Boston - Logan Airport and Boston Park Plaza. They're the first choice for many travelers to Great Barrington. If Hancock is next stop on your itinerary, Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel are two popular options.
How far in advance should I book my Western Massachusetts vacation?
It can be tricky to know when is the perfect time to book your trip to Western Massachusetts. But generally the earlier you book, the more affordable the prices. In some cases, you can lock in your flights and hotels up to 12 months prior to departure. If you're thinking of a last-minute getaway, no need to fret! There are incredible deals advertised on Expedia all the time.
What does an Expedia Western Massachusetts travel package include?
Hotels, flights and a reliable car for your road trip adventures. Simply mix and match your preferred bundle and get access to incredible deals. Once you've made your booking, add on a few activities and tours and watch your savings stack up. When it comes to planning your Western Massachusetts break, the choice is all yours!
What should I know before booking a Western Massachusetts travel package?
Whether it's relaxation or adventure you're chasing, a Western Massachusetts vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Western Massachusetts Expedia vacation package?
Yes, so take your pick! We offer more than 550 airlines worldwide, so you can customize your Western Massachusetts getaway according to your budget and style.
If I'm not able to travel, can I cancel my Western Massachusetts vacation package?
You can. We realize even the best-laid plans can go awry, so we're here to help if you have to make changes to your Western Massachusetts vacation package. You may be able to amend or cancel your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.