Western Massachusetts Vacation Packages 2026 from $746

Western Massachusetts flight + hotel vacation packages

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

The Yankee Inn

$746

per person

Jul 16 - Jul 21

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$1,853

per person

Aug 7 - Aug 11

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

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

Save 100% on your flight

$1,823

per person

Aug 7 - Aug 11

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

The Ponds at Foxhollow

$1,066

per person

Aug 7 - Aug 11

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

Prospect Berkshires

$1,394

per person

Aug 7 - Aug 11

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.

Top Western Massachusetts hotels deals

MGM Springfield

One MGM Way Springfield MA

$181 nightly

$205 total

May 31 - Jun 1

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

$128 nightly

$143 total

Jun 25 - Jun 26

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

Berkshires Untold

194 Pittsfield Rd Lenox MA

$119 nightly

$133 total

May 28 - May 29

Total with taxes and fees

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.

Pet friendly

Parking included

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$128 nightly

$143 total

May 28 - May 29

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

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$170 total

Jun 2 - Jun 3

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.

Pool

Hot Tub

Hotel UMass

1 Campus Center Way Amherst MA

$131 nightly

$147 total

Jun 3 - Jun 4

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

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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.

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.

A view of the University of Massachusetts campus

University of Massachusetts Amherst

4.5/5(262 reviews)

Enjoy the collegiate vibe when you visit University of Massachusetts Amherst, during your travels in Amherst. Experience the area's live music or attend a sporting event.

Frequently asked questions

How much are vacation packages to Western Massachusetts?

$746 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.