Book Exclusive Western Massachusetts Vacation Packages

Choose one or more items to build your trip:

Western Massachusetts flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $838, price is now CA $708 per person
CA $708
per person
Oct 9 - Oct 13
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Albany (ALB)
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

3.5 out of 5
Price was CA $1,270, price is now CA $1,012 per person
CA $1,012
per person
Oct 9 - Oct 13
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Albany (ALB)
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was CA $1,117, price is now CA $913 per person
CA $913
per person
Oct 9 - Oct 13
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Albany (ALB)
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was CA $1,132, price is now CA $971 per person
CA $971
per person
Oct 9 - Oct 13
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Albany (ALB)
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Hotel On North

Hotel On North

3.5 out of 5
Price was CA $1,378, price is now CA $1,199 per person
CA $1,199
per person
Oct 9 - Oct 13
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Albany (ALB)
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barrington Stage Company and Lichtenstein Center for the Arts are located nearby.

Top Western Massachusetts hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free cancellation
Reserve now, pay when you stay
The price is CA $175 per night
CA $175
CA $210 total
Jul 19 - Jul 20
includes taxes & fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Parking included
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free cancellation
The price is CA $226 per night
CA $226
CA $252 total
Aug 16 - Aug 17
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Massachusetts Museum of Contemporary Art and MCLA Gallery 51 are located nearby.
Pool
Hot tub
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free cancellation
The price is CA $166 per night
CA $166
CA $185 total
Aug 6 - Aug 7
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
Breakfast included
Parking included
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
The price is CA $237 per night
CA $237
CA $301 total
Aug 9 - Aug 10
includes taxes & fees
Stay at this hotel in Springfield. Enjoy free parking, an outdoor pool, and 8 restaurants. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags New England and MGM Springfield are located nearby.
Pool
Pet-friendly
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street Springfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $167 per night
CA $167
CA $190 total
Jul 19 - Jul 20
includes taxes & fees
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Six Flags New England and MGM Springfield are located nearby.
Pool
Breakfast included
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $215 per night
CA $215
CA $240 total
Jul 19 - Jul 20
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
Don't see what you're looking for?
See all available properties in Western Massachusetts
View all properties
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.

Stay near popular Western Massachusetts attractions

A roller coaster at an amusement park with a clear sky.

Six Flags New England

8.4/10 (599 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.
See properties

Frequently asked questions

How much are vacation packages to Western Massachusetts?
CA $708 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.

Photos of local treasures

Browse Western Massachusetts vacation photos for more inspiration

A lake with a rocky shoreline and a forested island.
A field of pumpkins surrounded by autumn leaves.
A panoramic view of a valley with autumn foliage, a town in the distance, and rolling hills.
A river winding through a valley with autumn foliage, surrounded by fields and distant hills.
An abandoned stone tower with graffiti, surrounded by leafless trees and snow.