
The Berkshires Vacation Packages
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3.0-star property
Berkshire Mountain Lodge
8.8/10 Excellent! (507 reviews)
Oct 9 - Oct 12
3 night stay
Washington (WAS) to Albany (ALB)
Southwest Airlines • Coach
Albany (ALB) to Washington (WAS)
American Airlines • Coach
per person
found 1 day ago
Great place and staff. Would stay again !!!!
Reviewed on May 22, 2025

3.5-star property
The Cornell Inn, Lenox & The Berkshires
9/10 Wonderful! (1,000 reviews)
Oct 9 - Oct 12
3 night stay
Washington (WAS) to Albany (ALB)
Southwest Airlines • Coach
Albany (ALB) to Washington (WAS)
American Airlines • Coach
Save 100% on your flight
per person
found 1 day 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 9 - Oct 12
3 night stay
Washington (WAS) to Albany (ALB)
Southwest Airlines • Coach
Albany (ALB) to Washington (WAS)
American Airlines • Coach
per person
found 1 day 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

3.5-star property
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
9/10 Wonderful! (667 reviews)
Oct 9 - Oct 12
3 night stay
Washington (WAS) to Albany (ALB)
Southwest Airlines • Coach
Albany (ALB) to Washington (WAS)
American Airlines • Coach
per person
found 1 day ago
Overall fun place to stay and enjoy the weekend.
Reviewed on May 28, 2024

3.0-star property
Club Wyndham Bentley Brook
9.2/10 Wonderful! (530 reviews)
Oct 9 - Oct 12
3 night stay
Washington (WAS) to Albany (ALB)
Southwest Airlines • Coach
Albany (ALB) to Washington (WAS)
American Airlines • Coach
per person
found 1 day 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 The Berkshires vacation package

Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
36.81 mi from city center
$144 nightly
The price is $160 total per night
$160 total
Sep 1 - Sep 2
Total includes taxes and fees
Guests of Hotel Downstreet, Ascend Hotel Collection have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The front desk is staffed 24 hours a day to help with luggage storage and securing valuables. Additional amenities include a hot tub, express check-out, and a vending machine.
Pool
Hot Tub

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
28.42 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

FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
21.05 mi from city center
$79 nightly
The price is $88 total per night
$88 total
Aug 3 - Aug 4
Total includes taxes and fees
Guests of FairBridge Inn Express enjoy access to free WiFi in public areas, meeting rooms, and a business center. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has laundry facilities.
Parking included
Free WiFi
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.
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