Western Massachusetts Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

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

Metro Center

1 out of top 10 points of interest in this area

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

Find hotels in Metro Center

Western Massachusetts Holiday

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 NZ$192 per night from 27 Aug to 28 Aug
NZ$192
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,929 reviews)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient"

Reviewed on 4 Aug. 2025

Vacation Village in the Berkshires
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
The price is NZ$306 per night from 25 Aug to 26 Aug
NZ$306
25 Aug - 26 Aug
includes taxes & fees
8.8/10 Excellent! (1,393 reviews)
"Everything was amazing, the only thing that the hotel rooms lacked was a mini fridge but other than that an amazing place to book a room!"

Reviewed on 3 Aug. 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! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"

Reviewed on 5 Aug. 2025

Get rates
Berkshire Mountain Lodge
See all 1,473 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.

Discover the most popular places to visit in Western Massachusetts

Hancock showing signage and autumn leaves

Jiminy Peak Mountain Resort

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this family-friendly area.

Jiminy Peak Mountain Resort
Norman Rockwell Museum

Norman Rockwell Museum

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

Williams College

Explore the campus of Williams College during your trip to Williamstown. In the area, take in the fascinating museums and mountain views.

Williams College

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