Western Massachusetts Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Western Massachusetts Holiday

With a Western Massachusetts holiday package, you can forget about the stress of planning and simply focus on experiencing everything this exciting destination has to offer. Start your trip to Western Massachusetts with a couple of days in Springfield visiting popular sights like Six Flags New England and MGM Springfield. Lenox is another top city that lures crowds from far and wide. National Shrine of the Divine Mercy and Norman Rockwell Museum are two of the top places to see in this destination. Whether you're planning to travel for a week or a month, Expedia are here to help you customise your next dream Western Massachusetts holiday.

Our guide on 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
A river with a bridge, a large dome-shaped building, and a cityscape with various buildings and roads.

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

Western Massachusetts Holiday

Western Massachusetts Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Top Sights
Mount Greylock, Bash Bish Falls State Park and Magic Wings Butterfly Conservatory

Our pick of the best Western Massachusetts 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
The price is AU$143 per night from 2 Nov to 3 Nov
AU$143
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (2,801 reviews)
"Our stay was great. The pictures don’t do this place justice. It exceeded our expectations. Will definitely be booking again in the future and take full advantage of amenities. Front desk clerk Joe was engaging and great to talk to."

Reviewed on 27 Oct 2026

Vacation Village in the Berkshires
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
The price is AU$273 per night from 1 Nov to 2 Nov
AU$273
1 Nov - 2 Nov
includes taxes & fees
MGM Springfield
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
The price is AU$176 per night from 8 Nov to 9 Nov
AU$176
8 Nov - 9 Nov
includes taxes & fees
Hotel UMass
See all 1,523 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Western Massachusetts attractions

A forested hillside with a clear path and a small building at the top.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)
Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.
See properties

Frequently asked questions

How much does a Western Massachusetts holiday package cost?
We make it simple for everyone to travel, with Western Massachusetts holiday packages starting from just . You'll have the flexibility to combine your favourite 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 travellers 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 holiday?
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 holiday package lets you organise 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 holiday 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 holiday package?
You can. We realise even the best-laid plans can go awry, so we're here to help if you have to make changes to your Western Massachusetts holiday 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.

Explore a world of travel with Expedia

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