
Western Massachusetts Vacation Packages
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3.0-star property
Vacation Village in the Berkshires
8.6/10 Excellent! (1,862 reviews)
Oct 3 - Oct 11
8 night stay
Calgary (YYC) to Albany (ALB)
American Airlines • Non-stop roundtrip • Coach
per person
found 20 hours ago
My husband and I stayed here for the last section of our vacation. The property was excellent-very clean & very quiet. Only thing was all parking was on gravel and on an angle so hard to find a safe spot for our motorcycle.
Reviewed on Jul 29, 2025

3.5-star property
The Cornell Inn, Lenox & The Berkshires
9/10 Wonderful! (1,000 reviews)
Oct 3 - Oct 11
8 night stay
Calgary (YYC) to Albany (ALB)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 20 hours ago
My wife and I dropped our daughter off at college, and were emotionally spent. I booked a room at The Cornell since it would be 2 hrs closer to home. Unbeknownst to me, this was just what we needed, and everything exceeded our expectations. The room, staff, and food were 2nd level.
Reviewed on Aug 27, 2024

3.0-star property
The Ponds at Foxhollow
8.6/10 Excellent! (121 reviews)
Oct 3 - Oct 11
8 night stay
Calgary (YYC) to Albany (ALB)
American Airlines • Non-stop roundtrip • Coach
per person
found 20 hours ago
The property is in a great location to explore The Berkshires. It could use some updating but some of the issues could be taken care of with little money - like newer towels in the bathroom, shower curtain, shower heads. Internet was terrible in the unit I was in, so was provided a booster. Maintenance staff is great. Had difficulty at check out because my payment to Orbitz hadn't been processed so the front desk staff wanted to charge me again. I made them call Orbitz and it was straightened out.
Reviewed on Dec 17, 2023

3.0-star property
Club Wyndham Bentley Brook
9.2/10 Wonderful! (530 reviews)
Oct 3 - Oct 11
8 night stay
Calgary (YYC) to Albany (ALB)
American Airlines • Non-stop roundtrip • Coach
per person
found 20 hours ago
We came to ski and this place was perfect! It’s a time share so it is set up for longer stays but we only stayed the weekend. Our two bed / two bath suite seemed to be recently renovated and was clean. A huge plus is that there were a few electric chargers and so that made things extra convenient. Only real negative thing we will say is that the pool water was cloudy and grayish. The hot tub water was brownish. This was after school vacation week so maybe it is due for a good cleaning?
Reviewed on Feb 23, 2025
Top rated hotels for your Western Massachusetts vacation package

MGM Springfield
One MGM Way, Springfield, MA
23.38 mi from city center
$159 nightly
The price is $180 total per night
$180 total
Aug 25 - Aug 26
Total includes taxes and fees
MGM Springfield features a casino, conference space, and a seasonal outdoor pool. A stay here includes free parking. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and dry cleaning/laundry. Additional amenities include express check-in, express check-out, and a gift shop.
Pool
Pet friendly

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
25.8 mi from city center
$106 nightly
The price is $119 total per night
$119 total
Aug 25 - Aug 26
Total includes taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included

Holiday Inn Express Springfield Downtown by IHG
145 State Street, Springfield, MA
Free Cancellation
23.3 mi from city center
$118 nightly
The price is $134 total per night
$134 total
Aug 3 - Aug 4
Total includes taxes and fees
Guests of Holiday Inn Express Springfield Downtown by IHG have access to an indoor pool, a gym, and free WiFi in public areas. A stay here includes free parking. Front-desk staff can answer questions 24/7, and assist with luggage storage, concierge services, and securing valuables. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
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