Western Massachusetts Vacation Packages 2026 from $499

Western Massachusetts flight + hotel vacation packages

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

Ambler Hotel

$499

per person

Sep 14 - Sep 17

found 9 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out is also provided.

The Cornell Inn, Lenox & The Berkshires

$962

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Gedney Farm

$722

per person

Sep 14 - Sep 18

found 19 hours ago

Roundtrip flight included

Houston (IAH) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.

Lodges At Cresthaven

$657

per person

Sep 14 - Sep 17

found 9 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

A restaurant and a 24-hour gym are featured at this lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A business center, a terrace, and a picnic area are also on offer.

The Whitlock

$697

per person

Sep 14 - Sep 18

found 19 hours ago

Roundtrip flight included

Houston (IAH) 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.

Top Western Massachusetts hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$150 total

Aug 18 - Aug 19

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.

Pool

Parking included

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

Aug 2 - Aug 3

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.

MGM Springfield

One MGM Way Springfield MA

$179 nightly

$203 total

Aug 9 - Aug 10

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

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free Cancellation

$118 nightly

$132 total

Aug 16 - Aug 17

Total with taxes and fees

A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.

Breakfast included

Parking included

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Free Cancellation

$142 nightly

$158 total

Jul 27 - Jul 28

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.

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$142 nightly

$158 total

Aug 23 - Aug 24

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)

Enjoy the rides and games at Six Flags New England and see why this is a favorite 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?

$499 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.