Western Massachusetts Vacations from $569
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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.
Gedney Farm
Price was $789, price is now $569 per person
$569
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (132 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.
Reviewed on Nov 2, 2025
Prospect Berkshires
Price was $1,103, price is now $740 per person
$740
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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
Pocketbook Hotel and Bath
Price was $927, price is now $664 per person
$664
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (3 reviews)
The front desk was very helpful in making sure we had a good stay.
Reviewed on Jan 9, 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
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint 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.
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.
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 19 to Jan 20
$141 total
Jan 19 - Jan 20
Total with taxes and fees
8.6/10 Excellent! (2,202 reviews)
Clean rooms, chimney did not work
Reviewed on Jan 4, 2026
MGM Springfield
One MGM Way Springfield MA
$145 nightly
The price is $165 total per night from Jan 19 to Jan 20
$165 total
Jan 19 - Jan 20
Total with taxes and fees
8.8/10 Excellent! (1,471 reviews)
Yes .. everything was excellent.
Reviewed on Jan 5, 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Jan 18 to Jan 19
$126 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (2,266 reviews)
The front staff upon arrival was incredibly kind and accommodating. We loved the pool and hot tub and the quiet, clean room. It was large and had everything we expected. The breakfast was also great- lots of options for everyone in our family! Thank you.
Reviewed on Jan 11, 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.