Western Massachusetts Vacations 2025/2026 from CA $1,247

Western Massachusetts flight + hotel packages

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

Valley Craft Ales

CA $1,247

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Stay at this lodge in Wilmington. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions South Main Street and Jim McGrath Gallery and Studio are located nearby.

The White House Inn

CA $1,381

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Stay at this 3.5-star hotel in Wilmington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.

Vacation Village in the Berkshires

CA $2,009

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Two Brooks Lodge

CA $1,925

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Stay at this 3-star vacation home in Bennington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Robert Frost Stone House Museum and Norman Rockwell Exhibition are located nearby.

Brook Bound Inn

CA $2,111

per person

Dec 24 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Albany (ALB)

Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.

Top Western Massachusetts hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free cancellation

Reserve now, pay when you stay

CA $128

CA $158 total

Nov 2 - Nov 3

includes taxes & fees

Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Pool

Parking included

MGM Springfield

One MGM Way, Springfield, MA

CA $222

CA $283 total

Nov 2 - Nov 3

includes taxes & fees

Stay at this 4-star hotel in Springfield. Enjoy free parking, an outdoor pool, and 8 restaurants. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags New England and MGM Springfield are located nearby.

Pool

Pet-friendly

La Quinta Inn & Suites by Wyndham Springfield MA

100 Congress Street, Springfield, MA

Free cancellation

Reserve now, pay when you stay

CA $166

CA $189 total

Oct 13 - Oct 14

includes taxes & fees

Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Six Flags New England and MGM Springfield are located nearby.

Pool

Breakfast included

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

Free cancellation

Reserve now, pay when you stay

CA $130

CA $176 total

Nov 2 - Nov 3

includes taxes & fees

Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

Pool

Hot tub

D. Hotel Suites & Spa

1 Country Club Rd, Holyoke, MA

Free cancellation

Reserve now, pay when you stay

CA $153

CA $178 total

Oct 22 - Oct 23

includes taxes & fees

Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Mount Tom State Reservation and Nash's Dinosaur Track Quarry are located nearby.

Pool

Hot tub

Holiday Inn Express Springfield Downtown by IHG

145 State Street, Springfield, MA

Free cancellation

CA $177

CA $201 total

Oct 19 - Oct 20

includes taxes & fees

Book a stay at this business-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Six Flags New England and MGM Springfield are located nearby.

Pool

Breakfast included

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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.

Popular places to visit

University of Massachusetts Amherst

4.5/5(7 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.

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

Naismith Memorial Basketball Hall of Fame

5/5(4 reviews)

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

5/5(6 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.

Frequently asked questions

How much are vacation packages to Western Massachusetts?

CA $1,247 is all you'll need for an exciting break in Western Massachusetts. Bundle your flights and hotel into a Travelocity package and see how much the savings pile up. With such good prices, you'll want to start packing your suitcase now!

Where can I get the best vacation package deals for Western Massachusetts?

There's no need to look any further than Travelocity. With as many as 400 air carriers and 1,000,000 worldwide properties, it's a breeze to find a Western Massachusetts package deal that fits your budget.

Why should I book my Western Massachusetts vacation bundle with Travelocity?

Because life is an amazing journey, and we offer all you need to help you along the way. With our first-rate service and Price Match Guarantee, you can book with confidence. What's more, you can rest easy while you're away knowing we've got your back with our round-the-clock support.

Can I save money on my Western Massachusetts car rental if I bundle it with hotels and flights?

You certainly can with our Western Massachusetts vacation packages. With one of these, there are loads of ways to stretch your vacation budget further. Bundle any two or more car, hotel, flight and tour bookings and see the savings add up. With your own ride, all the landmarks around Western Massachusetts are a fun road trip away.

Which airport is best for Western Massachusetts?

Bradley Intl. Airport (BDL) is where many visitors choose to touch down. Depending on your Western Massachusetts itinerary, Albany Intl. Airport (ALB) and Hartford, CT (HFD-Hartford - Brainard) are also worth considering.

What is there to do in Western Massachusetts?

Western Massachusetts is full of amazing things to see and do, however Naismith Memorial Basketball Hall of Fame and Six Flags New England are among the best of them.