The Berkshires Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top The Berkshires vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
9/10 Wonderful! (804 reviews)
Jan 25 - Jan 27
2 night stay
Cleveland (CLE) to Albany (ALB)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $472, price is now $416 per person
$416
per person
found 1 day ago
Staff is helpful and friendly!
Reviewed on Aug 11, 2025
3.5-star property
Gedney Farm
9.2/10 Wonderful! (132 reviews)
Jan 25 - Jan 27
2 night stay
Cleveland (CLE) to Albany (ALB)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $555, price is now $454 per person
$454
per person
found 1 day ago
Beautifully decorated and well-kept room and common areas. Looking forward to coming again!
Reviewed on Oct 13, 2022
2.0-star property
Wilder House Berkshires
9.8/10 Exceptional! (38 reviews)
Jan 25 - Jan 27
2 night stay
Cleveland (CLE) to Albany (ALB)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $544, price is now $464 per person
$464
per person
found 1 day ago
Beautiful property, super clean, close to great Barrington, and has EV charging, which was a plus. Can’t wait to visit again.
Reviewed on Oct 13, 2024
Top rated hotels for your The Berkshires vacation package
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
28.42 mi from city center
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
Total with 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
The Williams Inn
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
37.59 mi from city center
$186 nightly
The price is $208 total per night
$208 total
Dec 21 - Dec 22
Total with taxes and fees
At The Williams Inn, guests have access to a gym, free WiFi in public areas, and a conference center. If you drive, put free parking to good use. The front desk is staffed 24/7 to help with securing valuables, luggage storage, and concierge services. Additional amenities include coffee/tea in a common area, a terrace, and a ballroom.
Pet friendly
Parking included
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
20.16 mi from city center
$93 nightly
The price is $104 total per night
$104 total
Dec 21 - Dec 22
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly
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.
Explore More Ways to Travel with Travelocity
- Hotels near Otis Ridge
- 4 Star Hotels in Southfield
- B&B in Southfield
- Inns in Southfield
- Motels in Southfield
- Resorts in Southfield
- Villas in Southfield
- Cottages in New Marlborough
- Cheap Hotels in New Marlborough
- Hotels with Pool in New Marlborough
- Hotels with Bar in New Marlborough
- Pet Friendly Hotels in New Marlborough
- Ski Resorts & in New Marlborough
- Inns in New Marlborough
- Hotels near Bidwell House Museum
- B&B in Tolland
- Extended Stay Hotels in Tolland
- Tolland Hotels
- Hotels near Pyramid Lake
- B&B in Otis
- Cabin Rentals in Otis
- Guest Houses in Otis
- Pet Friendly Hotels in Otis
- Otis Hotels
- Motels in Otis
- Vacation Homes in Otis
- Rv Parks in Otis
- Resorts in Otis
- Hotels near Otis Reservoir
- Apartments in Mill River
- Motels in Mill River
- Town Houses in Mill River
- Hotels near Becket Land Trust Historic Quarry
- Hotels near Lee Premium Outlets
- 4 Star Hotels in Tyringham
- 5 Star Hotels in Tyringham
- B&B in Tyringham
- Cabin Rentals in Tyringham
- Cottages in Tyringham
- Hotels with Pool in Tyringham
- Lodges in Tyringham
- Rv Parks in Tyringham
- Resorts in Tyringham
- Hotels near Ashintully Gardens
- B&B in South Lee
- Cabin Rentals in South Lee
- Resorts in South Lee
- 3 Star Hotels in Monterey
- Apartments in Monterey
- B&B in Monterey
- Monterey Hotels
- Lodges in Monterey
- Motels in Monterey
- Vacation Homes in Monterey
- Rv Parks in Monterey
- Hotels near Jacob's Pillow
- Hotels near Les Trois Emme Winery
- Hotels near Ski Butternut
- Condo Rentals in Sandisfield
- Sandisfield Hotels
- Inns in Sandisfield
- Norman Rockwell Museum
- Hancock Vacations
- Kushi Institute
- West Springfield Vacations
- New Marlborough Vacations
- Holyoke Vacations
- Wyndhurst Golf & Club
- Big E
- Jiminy Peak Mountain Resort
- West Stockbridge Vacations
- Alford Vacations
- Lee Vacations
- Tolland State Forest
- Magnolia Bluffs Casino
- Berkshire Mountain Country Store
- Western Massachusetts Vacations
- Otis Reservoir
- Lenox Vacations
- Cheshire Vacations
- Great Barrington Vacations
- Chicopee Vacations
- Lee Premium Outlets
- Haydenville Vacations
- Ventfort Hall Mansion and Gilded Age Museum
- Stockbridge Vacations
- Northampton Vacations
- Tanglewood Music Center
- Westfield Vacations
- Southwick Vacations
- National Shrine of the Divine Mercy
