Western Massachusetts Vacation Packages 2026 from $695

Your Western Massachusetts Vacation

With a Western Massachusetts vacation 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 customize your next dream Western Massachusetts vacation.

The Latest Western Massachusetts vacation packages

Price found within the past 48 hours. Click for updated prices.

The Ponds at Foxhollow

Save 100% on your flight

$695

per person

Oct 22 - Oct 26

found 8 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

8.6/10 Excellent! (147 reviews)

Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely.

Reviewed on Sep 4, 2026

Prospect Berkshires

Save 100% on your flight

$1,791

per person

Oct 10 - Oct 17

found 7 hours ago

Roundtrip flight included

Tampa (TPA) to Albany (ALB)

10/10 Exceptional! (42 reviews)

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$906

per person

Oct 22 - Oct 26

found 4 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

9.2/10 Wonderful! (1,007 reviews)

Lodges At Cresthaven

$949

per person

Nov 13 - Nov 18

found 23 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Albany (ALB)

9.4/10 Exceptional! (629 reviews)

I love this place but was disappointed this trip. I will definitely go back with fingers crossed it will be better next time. The pool and playground were amazing for the kids, they loved it.

Reviewed on Sep 6, 2026

Quality Inn Lee - Lenox South

$830

per person

Oct 10 - Oct 17

found 8 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Albany (ALB)

8.4/10 Very Good! (1,009 reviews)

A clean, comfortable room close to Tanglewood. No complaints.

Reviewed on Sep 7, 2026

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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

Explore Springfield Armory National Park, Quadrangle museums, and enjoy over 70 clubs, bars, and restaurants in the Club Quarter. Exceptionally walkable, with easy access to I-91, I-291, and Union Station.

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

If you're spending some time in South End, Naismith Memorial Basketball Hall of Fame and Titanic Museum are top sights worth seeing.

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.

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

Sherwood Forest

While there might not be top attractions in Sherwood Forest, you can explore the larger area and discover places like Pyramid Lake and Jacob's Pillow.

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

Boston Road

While Boston Road might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lake Lorraine State Park and Chicopee Memorial State Park.

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 Harbor 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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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 Center Court, and immerse yourself in the game's rich history.

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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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A carousel with colorful decorations and a tall tower structure.

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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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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Western Massachusetts Hotel Deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

$122 nightly

$136 total

Sep 8 - Sep 9

Total with taxes and fees

8.8/10 Excellent! (2,611 reviews)

"X"

Reviewed on Sep 6, 2026

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

$143 nightly

$160 total

Sep 27 - Sep 28

Total with taxes and fees

MGM Springfield

One MGM Way Springfield MA

$179 nightly

$203 total

Sep 14 - Sep 15

Total with taxes and fees

See all 1,527 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.