Deals on vacations and trips to Western Massachusetts

Save when you book Western Massachusetts package deals

Choose two or more items and save on your trip:

Western Massachusetts flight + hotel vacation packages

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

Hideaway Inn Lenox

2 out of 5
Price was $945, price is now $683 per person
$683
per person
Aug 30 - Sep 3
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and picnic area. A communal living room, a library, and a virtual front desk are also on offer.
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Save 100% on your flight
Price was $3,551, price is now $2,604 per person
$2,604
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
A sauna, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room, a picnic area, and free newspapers are also on offer.
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,064, price is now $803 per person
$803
per person
Sep 4 - Sep 7
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Save 100% on your flight
Price was $968, price is now $738 per person
$738
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,438, price is now $1,101 per person
$1,101
per person
Aug 30 - Sep 3
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$143 nightly
The price is $159 total per night
$159 total
Jul 12 - Jul 13
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

MGM Springfield

4 out of 5
One MGM Way Springfield MA
$209 nightly
The price is $237 total per night
$237 total
Jul 9 - Jul 10
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
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $169 total per night
$169 total
Jul 9 - Jul 10
Total with taxes and fees
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.
Pool
Hot Tub
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Free Cancellation
$142 nightly
The price is $158 total per night
$158 total
Jul 12 - Jul 13
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
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
$180 nightly
The price is $201 total per night
$201 total
Jul 15 - Jul 16
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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$155 nightly
The price is $173 total per night
$173 total
Aug 6 - Aug 7
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
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?
$683 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.

Explore More Ways to Travel with Travelocity