Western Massachusetts Vacation Packages

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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.

Top Western Massachusetts Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was CA $1,211, price is now CA $1,030 per person
CA $1,030
per person
Oct 24 - Oct 27
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (129 reviews)
Rooting for them to make a go of this recently renovated hotel, but the experience was not what one would expect from a 4-star hotel. We had a corner room on a busy street and there was a lot of street noise that could be improved with double-paned windows. The room needed dusting, there was no bath gel in the shower, the walls are thin so could hear our 'neighbors', the kitchen floor needed a sweep, not terrible, but not without crumbs, and worst of all was the refrigerator which was very dirty. There was a slight smell of cooked food as though someone had been eating in there recently.

Reviewed on Sep. 3, 2025

Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
Price was CA $1,688, price is now CA $1,396 per person
CA $1,396
per person
Oct 6 - Oct 11
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (952 reviews)
They need to replenish the shampoo, conditioner and body lotion. The bottles were empty. The woman in the breakfast area was abusive. Trying to bump into me all the time.

Reviewed on Aug. 26, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
Price was CA $1,623, price is now CA $1,347 per person
CA $1,347
per person
Oct 6 - Oct 11
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.4/10 Very Good! (678 reviews)
First time staying there and it was great

Reviewed on Sep. 1, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was CA $1,702, price is now CA $1,441 per person
CA $1,441
per person
Oct 24 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (489 reviews)
Loved the lodge, beautiful grounds and convenience to downtown Lake George. Only con was that our lodge was near the maintenance shed, which at times was quite loud. This was a slight annoyance. Wouldn't stop me from booking again

Reviewed on Jul. 25, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was CA $1,386, price is now CA $1,182 per person
CA $1,182
per person
Oct 6 - Oct 11
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8/10 Very Good! (1,157 reviews)
Staff was inefficient and rude.

Reviewed on Aug. 31, 2025

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
Springfield showing heritage architecture

Metro Center

1 out of top 10 points of interest in this area
4/5(10 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.

Find hotels in Metro Center

Ready to book your vacation to Western Massachusetts?

 

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Western Massachusetts Hotel Deals

MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
The price is CA $219 per night from Oct 6 to Oct 7
CA $219
CA $280 total
Oct 6 - Oct 7
includes taxes & fees
MGM Springfield
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 11 to Sep 12
CA $210
CA $235 total
Sep 11 - Sep 12
includes taxes & fees
Hotel Downstreet, an Ascend Collection Hotel
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Sep 11 to Sep 12
CA $148
CA $180 total
Sep 11 - Sep 12
includes taxes & fees
Vacation Village in the Berkshires
See all 1,478 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Western Massachusetts

Springfield which includes interior views as well as a large group of people

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.

Naismith Memorial Basketball Hall of Fame
Eastern States Exposition

Eastern States Exposition

Enjoy an outing to Eastern States Exposition during your stay in West Springfield. You can attend a basketball game while in the area.

Eastern States Exposition
Norman Rockwell Museum

Norman Rockwell Museum

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

Frequently asked questions

Can I cancel my flight booking to Western Massachusetts due to COVID-19?
Our Customer Service Portal is where you can get information about changing or canceling your flight due to COVID-19. Before booking your tickets, it's a good idea to read the terms and conditions of your chosen airline too.
What's the best way to find cheap flights to Western Massachusetts that have flexible change policies?
At Expedia, we've been channeling our inner Olympic gymnast to get you the most flexible airfares in town. Simply tick the "No change fee" box directly below the filter heading "Flexible change policies" to find your ideal flight to Western Massachusetts.
What are some of the general tips for travelers to Western Massachusetts during the COVID-19 outbreak?
With new safety guidelines to adhere to, travel looks a bit different nowadays. Here are a few things to know before you head off to Western Massachusetts:
  • Investigate if any travel restrictions apply to your destination and origin before booking anything. Also check if there are any conditions you'll need to follow on arrival, such as taking a COVID-19 test.
  • Requirements state you must wear a face mask throughout your travel experience, even at screening checkpoints. Be ready to lower your mask for ID verification when asked.
  • Rather than handing a TSA officer your boarding pass, place it straight on the scanner yourself. After that, hold it up for inspection.
  • You're permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. You'll need to remove it for screening.
  • Place any personal items (e.g, wallet, keys and phone) in your carry-on instead of a bin to reduce handling during screening.
  • Transport any food items in a clear plastic bag and also put them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA employee will need to open your bag for inspection.

Which airlines fly to Western Massachusetts?
Cape Air operates flights into or near Western Massachusetts, including 1785 that fly into Logan Intl. Airport (BOS) each month. Pick your travel dates and then lock in your airfare early for the best price.
How can I find cheap tickets to Western Massachusetts?
Book well ahead, consider alternative airports, use frequent flyer miles — there's no shortage of ways! Another one is to make the most of Expedia's "flexible dates" function. Search for your Western Massachusetts flight, then check out the cheapest prices for nearby dates. In the last seven days, the best price for a flight to Western Massachusetts was .
How much is a flight to Western Massachusetts?
There were plenty of cheap fares for the taking in the last seven days, with the cost of a return airfare to Western Massachusetts varying between and . Many lucky vacationers scored one-way seats from () for only .
What are the most popular airports to fly into in Western Massachusetts?
A major gateway to Western Massachusetts, about 12051 flights land at Logan Intl. Airport (BOS) each month. Find an unbeatable deal, reserve your seat and get set to experience this popular region.
When is the cheapest time to fly to Western Massachusetts?
If you'd rather spend your hard-earned vacation money enjoying the best of Western Massachusetts rather than on flying there, depart earlier in the week. The most affordable day to fly is normally Tuesday, followed by Monday. With many people traveling on the weekend, Saturday tends to have the costliest ticket prices.
How much is a plane ticket to Western Massachusetts?
In the last seven days, ticket prices to Western Massachusetts ranged from to .
Which airlines with flights to Western Massachusetts employ COVID-19 cleanliness policies?
While traveling during an ongoing pandemic can be a challenging experience, airlines are doing their bit to protect the well-being of customers and crew. Here are a few carriers that have implemented changes:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.