Western Massachusetts Vacation Packages 2025/2026 from $396

Western Massachusetts flight + hotel vacation packages

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

Vacation Village in the Berkshires

Save 100% on your flight

per person

Oct 11 - Oct 18

found 24 hours ago

Roundtrip flight included

West Palm Beach (PBI) to Albany (ALB)

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.

Club Wyndham Bentley Brook

Save 100% on your flight

per person

Oct 11 - Oct 18

found 24 hours ago

Roundtrip flight included

West Palm Beach (PBI) to Albany (ALB)

Ski-in/ski-out access and an outdoor pool are featured at this smoke-free hotel. Take advantage of ski storage on site, and enjoy snowboarding. Enjoy the indoor pool and perks like free self parking and free WiFi.

The Yankee, Trademark Collection by Wyndham

Save 100% on your flight

per person

Oct 11 - Oct 18

found 24 hours ago

Roundtrip flight included

West Palm Beach (PBI) to Albany (ALB)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Prospect Berkshires

Save 100% on your flight

per person

Oct 11 - Oct 18

found 24 hours ago

Roundtrip flight included

West Palm Beach (PBI) to Albany (ALB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and concierge services are also on offer.

Top Western Massachusetts hotels deals

MGM Springfield

One MGM Way, Springfield, MA

$169 nightly

$192 total

Aug 11 - Aug 12

Total includes 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.

Holiday Inn Express Springfield Downtown by IHG

145 State Street, Springfield, MA

Free Cancellation

$114 nightly

$129 total

Aug 3 - Aug 4

Total includes 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

D. Hotel Suites & Spa

1 Country Club Rd, Holyoke, MA

Free Cancellation

$134 nightly

$150 total

Jul 27 - Jul 28

Total includes 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.

Hotel UMass

1 Campus Center Way, Amherst, MA

Free Cancellation

Reserve now, pay when you stay

$180 nightly

$201 total

Jul 23 - Jul 24

Total includes taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$123 total

Aug 4 - Aug 5

Total includes 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.

La Quinta Inn & Suites by Wyndham Springfield MA

100 Congress Street, Springfield, MA

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$129 total

Aug 3 - Aug 4

Total includes 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.

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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

4.5/5(255 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

4/5(130 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.

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

Tanglewood Music Center

5/5(150 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?

$396 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.