Western Massachusetts Vacation Packages 2026 from $765

Western Massachusetts flight + hotel vacation packages

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

Vacation Village in the Berkshires

$765

per person

Jul 29 - Aug 4

found 2 hours ago

Roundtrip non-stop flight included

Portland (PDX) 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 Yankee Inn

$938

per person

Jul 29 - Aug 4

found 2 hours ago

Roundtrip non-stop flight included

Portland (PDX) to Albany (ALB)

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.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

$957

per person

Jul 29 - Aug 4

found 2 hours ago

Roundtrip non-stop flight included

Portland (PDX) 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.

Berkshire Mountain Lodge

$823

per person

Jul 29 - Aug 4

found 2 hours ago

Roundtrip non-stop flight included

Portland (PDX) 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.

Bluebird Spa City Motor Lodge

Downtown Saratoga Springs

$1,275

per person

Jul 27 - Jul 31

found 4 hours ago

Roundtrip non-stop flight included

Albuquerque (ABQ) to Albany (ALB)

This hotel features free WiFi in public areas, concierge services, and self parking. Express check-out and luggage storage are also provided.

Top Western Massachusetts hotels deals

Hotel UMass

1 Campus Center Way Amherst MA

Free Cancellation

$130 nightly

$145 total

Jun 28 - Jun 29

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.

Breakfast included

Free WiFi

MGM Springfield

One MGM Way Springfield MA

$198 nightly

$224 total

Jun 14 - Jun 15

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

$149 nightly

$166 total

Jul 7 - Jul 8

Total with taxes and fees

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.

Pool

Parking included

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Free Cancellation

$142 nightly

$158 total

Jun 10 - Jun 11

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

$114 nightly

$129 total

Jul 6 - Jul 7

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

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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

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.

Tanglewood Music Center

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.

Wide paths in the middle pf a forest shows the ski trails on the mountains in the summer

Jiminy Peak Mountain Resort

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

Frequently asked questions

How much are vacation packages to Western Massachusetts?

$765 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.