Western Massachusetts Vacation Packages 2026 from $421

Western Massachusetts flight + hotel vacation packages

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

Hunters Grille and Tap at The Grafton Inn

$421

per person

Mar 6 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Worcester (ORH)

This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and a fireplace in the lobby are also provided.

Quality Inn & Suites Glenmont - Albany South

$615

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Fayetteville (FAY) to Albany (ALB)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Hampton Inn Albany-Wolf Road (Airport)

$455

per person

Apr 7 - Apr 9

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A computer station, dry cleaning, and luggage storage are also on offer.

Hilton Garden Inn Albany Airport

$491

per person

Apr 7 - Apr 9

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Albany (ALB)

This hotel features an indoor pool, A 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.

The Landing Hotel at Rivers Casino & Resort

Nothside

$431

per person

Apr 7 - Apr 9

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Albany (ALB)

A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.

Top Western Massachusetts hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$141 total

Jan 26 - Jan 27

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.

Pool

Parking included

MGM Springfield

One MGM Way Springfield MA

$145 nightly

$165 total

Jan 27 - Jan 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

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$139 total

Jan 26 - Jan 27

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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$136 total

Feb 22 - Feb 23

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

The Williams Inn

101 Spring Street Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$200 total

Jan 28 - Jan 29

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a coffee shop, and a terrace are also offered.

Pet friendly

Parking included

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$98 nightly

$109 total

Jan 30 - Jan 31

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

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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

A dip in the Outdoor heated pool before we hit the slopes

Jiminy Peak Mountain Resort

4.5/5(98 reviews)

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.

Basketball fans will love this museum, with all kinds of amazing displays about some of the greatest basketball players, games, stats, records, and basketball history.

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.

A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

Tanglewood Music Center

5/5(150 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?

$421 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.