Western Massachusetts Vacation Packages 2026 from $622

Western Massachusetts flight + hotel vacation packages

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

Hotel Vienna

$622

per person

Jul 20 - Jul 25

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Hudson (HCC)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.

Urban Cowboy Lodge

Save 100% on your flight

$1,062

per person

Jul 20 - Jul 25

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Albany (ALB)

This lodge features a restaurant, a sauna, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, a lobby fireplace, and a communal living room are also on offer.

The Wiltwyck

$762

per person

Jul 20 - Jul 25

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Albany (ALB)

Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Save 100% on your flight

$6,449

per person

Jul 20 - Jul 25

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Hudson (HCC)

Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Save 100% on your flight

$6,513

per person

Jul 20 - Jul 25

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Hudson (HCC)

An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A terrace is also provided.

Top Western Massachusetts hotels deals

Hotel UMass

1 Campus Center Way Amherst MA

Free Cancellation

$126 nightly

$140 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.

Breakfast included

Free WiFi

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Free Cancellation

$163 nightly

$182 total

Jun 14 - Jun 15

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

MGM Springfield

One MGM Way Springfield MA

$229 nightly

$260 total

Jun 17 - Jun 18

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.

Pool

Parking included

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.

Pool

Hot Tub

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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?

$622 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.