Western Massachusetts Vacations from $760
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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
Save 100% on your flight
Price was $1,188, price is now $760 per person
$760
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.6/10 Exceptional! (4 reviews)
I had an absolutely amazing time here, it is even more beautiful than the pictures. Where do I begin! Right from the start we were greeted by welcoming staff who gave us a tour of the property on a golf cart as we reached our cabin. Golf carts are offered and easily available for a lift to anywhere within the property that you’d like. The shower pressure was perfect and hot as well. Our cabin was curated to feel cozy and came equipped with beach chairs, umbrellas and beach towels. The saunas and locker rooms were beautifully made. We enjoyed spending timing at the lake going kayaking as well and then sitting at the fire pit to star gaze. We also enjoyed playing pickleball/tennis at the court. My only quip would be that the pool water is still quite cool despite being heated. The whole property is an experience in itself. You can tell it was produced with a lot of meticulous attention to detail. I am already dreaming of when I can come back here!
Reviewed on Sep 27, 2025
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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
1 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
University of Massachusetts Amherst
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.
Naismith Memorial Basketball Hall of Fame
You can study the exhibits at Naismith Memorial Basketball Hall of Fame, a museum with a storied past, during your trip to Springfield. You can attend a basketball game while in the area.
Tanglewood Music Center
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
$112 nightly
The price is $125 total per night from Oct 30 to Oct 31
$125 total
Oct 30 - Oct 31
Total with taxes and fees
8.6/10 Excellent! (2,049 reviews)
Check-in Needs Improvement
"Why have an on-line pre-check process if you have to wait in a long line when you arrive. Need to have separate line(s) for those who pre-check."
Reviewed on Oct 11, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $130 total per night from Nov 11 to Nov 12
$130 total
Nov 11 - Nov 12
Total with taxes and fees
8/10 Very Good! (1,290 reviews)
"Hotel was under renovation. Experience would have been better after the improvements."
Reviewed on Oct 12, 2025
Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
$137 nightly
The price is $153 total per night from Nov 11 to Nov 12
$153 total
Nov 11 - Nov 12
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
Reviewed on Oct 9, 2025
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.
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.