Western Massachusetts Vacations 2026 from CA $992

Western Massachusetts flight + hotel packages

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

Berkshire Mountain Lodge

CA $992

per person

Jul 14 - Jul 17

found 4 hours ago

Roundtrip non-stop flight included

St. John's (YYT) to Albany (ALB)

Book a stay at this 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.

The Wiltwyck

CA $1,685

per person

Aug 13 - Aug 19

found 19 hours ago

Roundtrip flight included

Montreal (YUL) to Albany (ALB)

Stay at this guesthouse in Kingston. Enjoy free WiFi, free parking, and Netflix. Popular attractions Senate House State Historic Site and Volunteer Fireman's Hall and Museum of Kingston are located nearby.

The Hideout Catskills Cottage

CA $2,394

per person

Aug 13 - Aug 19

found 19 hours ago

Roundtrip flight included

Montreal (YUL) to Albany (ALB)

Stay at this vacation home in Kingston. Enjoy free parking and a garden. Popular attractions Rosendale Trestle and Rosendale Public Library are located nearby.

Vacation Village in the Berkshires

CA $1,058

per person

Jul 15 - Jul 19

found 12 hours ago

Roundtrip non-stop flight included

Windsor (YQG) to Albany (ALB)

Book a stay at this 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.

Berkshires Untold

CA $1,149

per person

Jul 14 - Jul 17

found 4 hours ago

Roundtrip non-stop flight included

St. John's (YYT) to Albany (ALB)

Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.

Top Western Massachusetts hotels deals

MGM Springfield

One MGM Way Springfield MA

CA $246

CA $310 total

Jun 14 - Jun 15

includes taxes & fees

Stay at this 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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $168

CA $219 total

Jun 4 - Jun 5

includes taxes & fees

Pool

Hot tub

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

CA $165

CA $199 total

Jun 4 - Jun 5

includes taxes & fees

Pool

Parking included

Hotel UMass

1 Campus Center Way Amherst MA

CA $167

CA $188 total

Jun 30 - Jul 1

includes taxes & fees

Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and 5 coffee shops/cafes. Our guests praise the helpful staff in our reviews. Popular attractions Mullins Center and UMass Fine Arts Center are located nearby.

Breakfast included

Free WiFi

Holiday Inn Express Springfield Downtown by IHG

145 State Street Springfield MA

Free cancellation

Reserve now, pay when you stay

CA $179

CA $203 total

Jun 22 - Jun 23

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

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

CA $142

CA $166 total

Jun 14 - Jun 15

includes taxes & fees

Book a stay at this 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

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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

Six Flags New England

Enjoy the rides and games at Six Flags New England and see why this is a favorite amusement park in Agawam. 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.

Wide paths in the middle pf a forest shows the ski trails on the mountains in the summer

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.

Frequently asked questions

How much are vacation packages to Western Massachusetts?

CA $992 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.