Western Massachusetts Vacation Packages 2026 from $684

Western Massachusetts flight + hotel vacation packages

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

Berkshire Mountain Lodge

$684

per person

Aug 27 - Aug 30

found 20 hours ago

Roundtrip non-stop flight included

Miami (MIA) 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.

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$1,304

per person

Aug 27 - Aug 30

found 20 hours ago

Roundtrip non-stop flight included

Miami (MIA) 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 Ponds at Foxhollow

$908

per person

Aug 27 - Aug 30

found 20 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Albany (ALB)

This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and conveniences like a terrace and laundry facilities.

The Whitlock

$938

per person

Aug 27 - Aug 30

found 20 hours ago

Roundtrip non-stop flight included

Miami (MIA) 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.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

$1,457

per person

Aug 27 - Aug 30

found 20 hours ago

Roundtrip non-stop flight included

Miami (MIA) to Albany (ALB)

This cottage includes free WiFi in public areas and barbecue grills.

Top Western Massachusetts hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$169 total

Jul 19 - Jul 20

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.

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free Cancellation

$161 nightly

$179 total

Aug 16 - Aug 17

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 free perks like continental breakfast and free self parking.

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Free Cancellation

$118 nightly

$132 total

Aug 6 - Aug 7

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.

MGM Springfield

One MGM Way Springfield MA

$199 nightly

$226 total

Jul 19 - Jul 20

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.

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

Jul 19 - Jul 20

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.

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$211 total

Jul 19 - Jul 20

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.

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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.

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Frequently asked questions

How much are vacation packages to Western Massachusetts?

$684 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.