Western Massachusetts Vacations 2025/2026 from CA $1,131

Western Massachusetts flight + hotel packages

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

Trainmasters Inn

CA $1,131

per person

Feb 11 - Feb 18

found 13 hours ago

Roundtrip flight included

Vancouver (YVR) to Worcester (ORH)

Stay at this B&B in Palmer. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Chase Memorial Park and Yankee Flea Market are located nearby.

Vacation Village in the Berkshires

CA $1,391

per person

Dec 24 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) 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.

The White House Inn

CA $1,570

per person

Dec 24 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Albany (ALB)

Stay at this 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.

The Landing Hotel at Rivers Casino & Resort

Stockade Historic District

CA $1,315

per person

Dec 24 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Albany (ALB)

Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Scene One Movieland are located nearby.

The Equinox Golf Resort & Spa

CA $1,492

per person

Dec 20 - Dec 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing 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 $104

CA $131 total

Nov 23 - Nov 24

includes taxes & fees

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.

Pool

Parking included

MGM Springfield

One MGM Way Springfield MA

CA $190

CA $247 total

Nov 23 - Nov 24

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 MGM Springfield and Six Flags New England 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 $155

CA $175 total

Nov 25 - Nov 26

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 MGM Springfield and Six Flags New England are located nearby.

Pool

Breakfast included

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

Get rates

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 Guido's Marketplace and Herman Melville's Arrowhead are located nearby.

Pool

Hot tub

Holiday Inn Express Springfield Downtown by IHG

145 State Street Springfield MA

Free cancellation

CA $145

CA $168 total

Dec 8 - Dec 9

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 MGM Springfield and Six Flags New England are located nearby.

Pool

Breakfast included

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Free cancellation

Reserve now, pay when you stay

CA $154

CA $179 total

Nov 23 - Nov 24

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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See all available properties in Western Massachusetts

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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

Hancock which includes signage and autumn leaves

Jiminy Peak Mountain Resort

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this family-friendly area.

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.

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.

Frequently asked questions

How much are vacation packages to Western Massachusetts?

CA $1,131 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.