Western Massachusetts Holidays

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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
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.

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A basketball court with spectators, a scoreboard, and a wall of portraits.

South End

1 out of top 10 points of interest in this area

While visiting South End, you might make a stop by sights like Naismith Memorial Basketball Hall of Fame and Titanic Museum.

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A dense forest with a stream, moss-covered rocks, and ferns.

Forest Park

While visiting Forest Park, you might make a stop by sights like Forest Park and Zoo in Forest Park and Education Center.

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A snow-covered park with a gazebo, a bench, and bare trees.

Boston Road

Though Boston Road may not have many top sights, you can venture to the surrounding area to see attractions like Lake Lorraine State Park and Chicopee Memorial State Park.

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A calm lake surrounded by autumn-colored trees reflecting the sky.

Sherwood Forest

When in Sherwood Forest, you can plan a visit to Pyramid Lake and Jacob's Pillow, some noteworthy sights in the nearby area.

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Top hotels in Western Massachusetts

Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
S$150
23 Sept - 24 Sept
includes taxes & fees
8.8/10 Excellent! (2,667 reviews)
"Great place to stay in the Berkshires in the summer! Best price in the area for a busy weekend at Tanglewood. All other options were ridiculously expensive, Resort had great amenities. The indoor pool and outdoor hot tub where much appreciated after our trip out from the Boston area. Highly recommend ..."

Reviewed on 22 Sept, 2026

Vacation Village in the Berkshires
MGM Springfield

MGM Springfield

One MGM Way Springfield MA
S$249
8 Oct - 9 Oct
includes taxes & fees
MGM Springfield
Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

145 State Street Springfield MA
Fully refundableReserve now, pay when you stay
S$145
21 Oct - 22 Oct
includes taxes & fees
9/10 Wonderful! (1,303 reviews)
"Did not like the parking. Lot of construction in the area. Safety to from the assigned parking was a concern at times. The rain didn't help the situation either. During the construction period a small shuttle to the parking lot would help. A multi passenger golf cart would be ideal."

Reviewed on 21 Sept, 2026

Holiday Inn Express Springfield Downtown by IHG
See all 1,524 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.

Stay near popular Western Massachusetts attractions

A roller coaster at an amusement park with a clear sky.

Six Flags New England

8.4/10 (599 reviews)
New England's largest amusement park thrills with 11 roller coasters, including the top-rated Superman The Ride. Experience heart-pounding drops on Wicked Cyclone, or cool off at Hurricane Harbour water park.
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A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)
Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.
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A hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.

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.
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A basketball court with spectators, a scoreboard, and a wall of portraits.
Photo by Groovy Trip

Naismith Memorial Basketball Hall of Fame

8.6/10 (481 reviews)
The Basketball Hall of Fame celebrates the sport's greatest legends in Springfield, basketball's birthplace. Explore interactive exhibits, test your skills on Centre Court, and immerse yourself in the game's rich history.
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A carousel with colorful decorations and a tall tower structure.
Photo by Jennifer Brokaw

Eastern States Exposition

8.4/10 (260 reviews)
New England's largest fair, The Big E draws 1.6 million visitors annually with agricultural exhibits and entertainment. Explore the Avenue of States and Storrowton Village while sampling diverse regional cuisine.
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A snowy cityscape with various buildings and a large sports stadium.

Amherst College

9.2/10 (300 reviews)
Explore Amherst College's historic College Row and impressive art and natural history museums. Wander through the tranquil Yushien Japanese Garden or attend one of the many public cultural events on campus.
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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)
Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.
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Eastern States Exposition

8.6/10 (302 reviews)
This beloved New England fair showcases all six states' cultures through exhibits, food, and entertainment. Explore the Avenue of States, sample iconic cream puffs, or catch a live concert during its September run.
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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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.