Western Massachusetts Vacation Packages 2025/2026 from $395

Western Massachusetts flight + hotel vacation packages

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

Residence Inn by Marriott Kingston

$395

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.

AutoCamp Catskills

$405

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Houston (IAH) to Hudson (HCC)

A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Save 100% on your flight

$720

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

The Wiltwyck

$422

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.

The Leeway

$513

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

This motel features a garden, barbecue grills, and free self parking. A picnic area, express check-out, and a virtual front desk are also on offer.

Top Western Massachusetts hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$143 total

Oct 1 - Oct 2

Total with taxes and fees

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Parking included

MGM Springfield

One MGM Way, Springfield, MA

$179 nightly

$203 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features a casino and 8 restaurants. Relax with a drink at one of the 5 bars/lounges and enjoy perks like free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a coffee shop are also provided.

Pool

Pet friendly

La Quinta Inn & Suites by Wyndham Springfield MA

100 Congress Street, Springfield, MA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$135 total

Oct 13 - Oct 14

Total with taxes and fees

This hotel features an indoor pool and a gym. Families will appreciate the arcade/game room and onsite laundry facilities. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking.

Pool

Breakfast included

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield, MA

$128 nightly

$143 total

Oct 1 - Oct 2

Total with taxes and fees

This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.

Pool

Hot Tub

D. Hotel Suites & Spa

1 Country Club Rd, Holyoke, MA

$134 nightly

$150 total

Oct 1 - Oct 2

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry facilities.

Pool

Hot Tub

Holiday Inn Express Springfield Downtown by IHG

145 State Street, Springfield, MA

Free Cancellation

$127 nightly

$144 total

Oct 7 - Oct 8

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

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

Great bar and restaurant in a great area in Venice. Bar in front, restaurant tables al fresco in back; very cool. Good food, and hand crafted cocktails by a talented and enthusiastic staff.

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.

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.

A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

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?

$395 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.