Western Massachusetts Vacations from $425
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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.
Prospect Berkshires
Price was $799, price is now $429 per person
$429
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.
Reviewed on Nov 29, 2025
The Equinox Golf Resort & Spa
Manchester Village Historic District
Save 100% on your flight
Price was $2,071, price is now $1,438 per person
$1,438
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
7.4/10 Good! (567 reviews)
Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral.
One front desk person directed me to closed restaurants...
Reviewed on Jan 9, 2026
The Manchester View
Price was $1,011, price is now $702 per person
$702
per person
Feb 13 - Feb 18
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.4/10 Exceptional! (772 reviews)
The place is great. Especially the wood burning stove in the room.
Reviewed on Jan 7, 2026
Aspen At Manchester
Price was $896, price is now $692 per person
$692
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (600 reviews)
Everything was good, The refrigerator was barely working, so we had to take the food outside.
Reviewed on Jan 7, 2026
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View all tripsWhere to stay in Western Massachusetts
Find the best Western Massachusetts areas and neighborhoods for the activities you enjoy most. Learn more about Western Massachusetts
Metro Center
2 out of top 10 points of interest in this area
3.5/5(242 area reviews)
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.
Discover the most popular places to visit in Western Massachusetts
Jiminy Peak Mountain Resort
4.5/5(98 reviews)
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.
University of Massachusetts Amherst
4.5/5(255 reviews)
Enjoy the collegiate vibe when you visit University of Massachusetts Amherst, during your travels in Amherst. Experience the area's live music or attend a sporting event.
Tanglewood Music Center
5/5(150 reviews)
You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.
Western Massachusetts Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Jan 11 to Jan 12
$141 total
Jan 11 - Jan 12
Total with taxes and fees
8.6/10 Excellent! (2,200 reviews)
Clean rooms, chimney did not work
Reviewed on Jan 4, 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Jan 21 to Jan 22
$118 total
Jan 21 - Jan 22
Total with taxes and fees
9.2/10 Wonderful! (2,262 reviews)
The staff was super helpful and courteous. The room and public areas were superb. We did not use the pool but the area was neatly kept and very attractive (brightly colored and well lit). The hotel is located in a safe area, surrounded by woods, and overlooking the Connecticut River.
Reviewed on Jan 6, 2026
MGM Springfield
One MGM Way Springfield MA
$154 nightly
The price is $175 total per night from Jan 11 to Jan 12
$175 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,471 reviews)
Yes .. everything was excellent.
Reviewed on Jan 5, 2026
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.
Find the Best Western Massachusetts Vacation Packages
Western Massachusetts Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Logan Intl. Airport (BOS) |
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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.
