Western Massachusetts Vacation Packages 2026 from $359

Western Massachusetts flight + hotel vacation packages

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

Holiday Inn Club Vacations Oak 'n Spruce Resort

$359

per person

Oct 30 - Nov 1

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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

$657

per person

Oct 16 - Oct 22

found 1 day ago

Roundtrip 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 Whitlock

$444

per person

Oct 30 - Nov 1

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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.

Spacious Home in Troy

$837

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

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

Berkshire Mountain Lodge

$363

per person

Oct 30 - Nov 1

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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.

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

Pool

Parking included

MGM Springfield

One MGM Way Springfield MA

$179 nightly

$203 total

Aug 20 - Aug 21

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

Free Cancellation

$142 nightly

$158 total

Aug 17 - Aug 18

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

$104 nightly

$118 total

Sep 14 - Sep 15

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.

Pool

Breakfast included

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.

Pool

Hot Tub

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$139 total

Aug 31 - Sep 1

Total with taxes and fees

Don't see what you're looking for?

See all available properties in Western Massachusetts

View all properties

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?

$359 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.