Western Massachusetts Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Tu Nguyen

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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

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

2 out of top 10 points of interest in this area

If you're spending some time in Metro Center, Paramount Theater and CityStage Symphony Hall 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
The price is NZ$221 per night from 4 Jan to 5 Jan
NZ$221
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,179 reviews)
My stay was great with no problems.

Reviewed on 19 Dec 2025

Vacation Village in the Berkshires
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
The price is NZ$333 per night from 4 Jan to 5 Jan
NZ$333
4 Jan - 5 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,455 reviews)
The check-in was smooth and easy. The room was clean and well decorated. The room is was not basic beige, it was stylish. The beds and pillows were very comfortable.

Reviewed on 20 Dec 2025

MGM Springfield
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is NZ$220 per night from 1 Jan to 2 Jan
NZ$220
1 Jan - 2 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (2,259 reviews)
Everything was perfect.

Reviewed on 17 Dec 2025

D. Hotel Suites & Spa
See all 1,478 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 quaint area.

Jiminy Peak Mountain Resort

Ski Butternut

Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.

Ski Butternut

National Shrine of the Divine Mercy

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

National Shrine of the Divine Mercy

Frequently asked questions

Can I cancel my flight booking to Western Massachusetts due to COVID-19?
Our Customer Service Portal is where you can get information about changing or cancelling your flight due to COVID-19. Before booking your tickets, it's a good idea to read the terms and conditions of your chosen airline too.
What's the best way to find cheap flights to Western Massachusetts that have flexible change policies?
At Expedia, we've been channeling our inner Olympic gymnast to get you the most flexible airfares in town. Simply tick the "No change fee" box directly below the filter heading "Flexible change policies" to find your ideal flight to Western Massachusetts.
What are some of the general tips for travellers to Western Massachusetts during the COVID-19 outbreak?
With new safety guidelines to adhere to, travel looks a bit different nowadays. Here are a few things to know before you head off to Western Massachusetts:
  • Investigate if any travel restrictions apply to your destination and origin before booking anything. Also check if there are any conditions you'll need to follow on arrival, such as taking a COVID-19 test.
  • Requirements state you must wear a face mask throughout your travel experience, even at screening checkpoints. Be ready to lower your mask for ID verification when asked.
  • Rather than handing a TSA officer your boarding pass, place it straight on the scanner yourself. After that, hold it up for inspection.
  • You're permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. You'll need to remove it for screening.
  • Place any personal items (e.g, wallet, keys and phone) in your carry-on instead of a bin to reduce handling during screening.
  • Transport any food items in a clear plastic bag and also put them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA employee will need to open your bag for inspection.

Which airlines fly to Western Massachusetts?
Cape Air operates flights into or near Western Massachusetts, including 1785 that fly into Logan Intl. Airport (BOS) each month. Pick your travel dates and then lock in your airfare early for the best price.
How can I find cheap tickets to Western Massachusetts?
Book well ahead, consider alternative airports, use frequent flyer miles — there's no shortage of ways! Another one is to make the most of Expedia's "flexible dates" function. Search for your Western Massachusetts flight, then check out the cheapest prices for nearby dates. In the last seven days, the best price for a flight to Western Massachusetts was .
How much is a flight to Western Massachusetts?
There were plenty of cheap fares for the taking in the last seven days, with the cost of a return airfare to Western Massachusetts varying between and . Many lucky holiday makers scored one-way seats from () for only .
What are the most popular airports to fly into in Western Massachusetts?
A major gateway to Western Massachusetts, about 12051 flights land at Logan Intl. Airport (BOS) each month. Find an unbeatable deal, reserve your seat and get set to experience this popular region.
When is the cheapest time to fly to Western Massachusetts?
If you'd rather spend your hard-earned holiday money enjoying the best of Western Massachusetts rather than on flying there, depart earlier in the week. The most affordable day to fly is normally Tuesday, followed by Monday. With many people travelling on the weekend, Saturday tends to have the costliest ticket prices.
How much is a plane ticket to Western Massachusetts?
In the last seven days, ticket prices to Western Massachusetts ranged from to .
Which airlines with flights to Western Massachusetts employ COVID-19 cleanliness policies?
While travelling during an ongoing pandemic can be a challenging experience, airlines are doing their bit to protect the well-being of customers and crew. Here are a few carriers that have implemented changes:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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.