Western Massachusetts Vacation Packages 2026 from $554

Western Massachusetts flight + hotel vacation packages

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

Vacation Village in the Berkshires

$554

per person

Jul 16 - Jul 19

found 21 hours ago

Roundtrip flight included

Chicago (ORD) 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.

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$1,759

per person

Jul 16 - Jul 19

found 21 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Quality Inn Lee - Lenox South

$724

per person

Jul 16 - Jul 19

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the express check-in. A restaurant, a 24-hour front desk, and express check-out are also provided.

Best Western Plus Berkshire Hills Inn & Suites

$799

per person

Jul 16 - Jul 19

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

$1,649

per person

Jul 16 - Jul 19

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Albany (ALB)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Top Western Massachusetts hotels deals

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free Cancellation

$161 nightly

$180 total

Jun 15 - Jun 16

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.

Hotel UMass

1 Campus Center Way Amherst MA

Free Cancellation

$144 nightly

$161 total

Jul 2 - Jul 3

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.

MGM Springfield

One MGM Way Springfield MA

$229 nightly

$260 total

Jun 22 - Jun 23

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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$173 total

Jun 14 - Jun 15

Total with taxes and fees

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.

Pool

Hot Tub

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$152 total

Jun 14 - Jun 15

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.

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Free Cancellation

$142 nightly

$158 total

Jun 14 - Jun 15

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.

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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)

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.

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.

Tanglewood Music Center

5/5(152 reviews)

You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.

Frequently asked questions

How much are vacation packages to Western Massachusetts?

$554 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.