Western Massachusetts Vacation Packages 2026 from $380

Western Massachusetts flight + hotel vacation packages

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

Vacation Village in the Berkshires

$380

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Albany (ALB)

This aparthotel 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.

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$784

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

The Whitlock

$745

per person

Oct 28 - Nov 2

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.

Berkshire Mountain Lodge

$395

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Albany (ALB)

This aparthotel 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 Express & Suites Pittsfield-Lenox-Berkshires by IHG

$477

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) 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 hot tub and free perks like buffet breakfast and free self parking.

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

Aug 31 - Sep 1

Total with taxes and fees

This aparthotel 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.

MGM Springfield

One MGM Way Springfield MA

$179 nightly

$203 total

Aug 27 - Aug 28

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

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

$142 nightly

$158 total

Aug 23 - Aug 24

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

Reserve now, pay when you stay

$118 nightly

$134 total

Sep 8 - Sep 9

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. Enjoy the free on-the-go breakfast each morning.

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$158 nightly

$176 total

Sep 14 - Sep 15

Total with taxes and fees

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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$125 nightly

$139 total

Aug 31 - Sep 1

Total with taxes and fees

This aparthotel 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.

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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.

Stay near popular Western Massachusetts attractions

A roller coaster at an amusement park with a clear sky.

Six Flags New England

8.4/10 (599 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.

See properties

Frequently asked questions

How much are vacation packages to Western Massachusetts?

$380 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.