Western Massachusetts Vacation Packages 2026 from $374

Western Massachusetts flight + hotel vacation packages

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

Berkshire Mountain Lodge

$374

per person

May 29 - Jun 1

found 8 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

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.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

$430

per person

May 29 - Jun 1

found 8 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.

Vacation Village in the Berkshires

$384

per person

May 29 - Jun 1

found 8 hours ago

Roundtrip flight included

Denver (DEN) 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.

Berkshires Untold

$498

per person

May 29 - Jun 1

found 8 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.

Hampton Inn & Suites Berkshires-Lenox

$475

per person

May 29 - Jun 1

found 8 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

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 buffet breakfast and free self parking.

Top Western Massachusetts hotels deals

MGM Springfield

One MGM Way Springfield MA

$209 nightly

$237 total

May 10 - May 11

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

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free Cancellation

$142 nightly

$158 total

May 19 - May 20

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$123 total

Apr 30 - May 1

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

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Free Cancellation

$150 nightly

$168 total

May 3 - May 4

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

Hotel UMass

1 Campus Center Way Amherst MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$135 total

May 10 - May 11

Total with taxes and fees

This hotel features 5 coffee shops/cafes and a bar/lounge. Enjoy a meal from the restaurant and perks like free continental breakfast and free WiFi. Self parking, a snack bar/deli, and a lobby fireplace are also offered.

Breakfast included

Free WiFi

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$103 total

May 4 - May 5

Total with taxes and fees

Pet friendly

Parking 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

Six Flags New England

4/5(210 reviews)

Bring the kids to Six Flags New England and enjoy the excitement of this amusement park in Agawam. You can attend a basketball game while in the area.

A view of the University of Massachusetts campus

University of Massachusetts Amherst

4.5/5(262 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.

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.

Frequently asked questions

How much are vacation packages to Western Massachusetts?

$374 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.