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
The Cornell Inn, Lenox & The Berkshires
9.2/10 Wonderful! (1,002 reviews)
Sep 24 - Sep 27
3 night stay
Fort Lauderdale (FLL) to Albany (ALB)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,083, price is now $763 per person
$763
per person
found 1 day ago
The staff were terrific from welcome to departure. Breakfast was diverse and tasty. The Inn location was great for Tanglewood and local restaurants. We intend to return should we be in that area again!
Reviewed on Aug 12, 2026
3.0-star property
Prospect Berkshires
9.8/10 Exceptional! (40 reviews)
Oct 18 - Oct 22
4 night stay
Fort Lauderdale (FLL) to Albany (ALB)
JetBlue Airways • Coach
Albany (ALB) to Fort Lauderdale (FLL)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,432, price is now $1,040 per person
$1,040
per person
found 18 hours ago
Once I got the cabin I expected it was an amazing stay.
Right on the water as shown on the website.
I look forward to my next stay.
Reviewed on Aug 1, 2026
3.0-star property
The Ponds at Foxhollow
8.6/10 Excellent! (145 reviews)
Oct 18 - Oct 22
4 night stay
Fort Lauderdale (FLL) to Albany (ALB)
JetBlue Airways • Coach
Albany (ALB) to Fort Lauderdale (FLL)
Southwest Airlines • Coach
Price was $863, price is now $656 per person
$656
per person
found 18 hours ago
Quiet property. Convenient location.
Reviewed on Aug 2, 2026
3.5-star property
Gedney Farm
9.2/10 Wonderful! (140 reviews)
Oct 18 - Oct 22
4 night stay
Fort Lauderdale (FLL) to Albany (ALB)
JetBlue Airways • Coach
Albany (ALB) to Fort Lauderdale (FLL)
Southwest Airlines • Coach
Price was $811, price is now $619 per person
$619
per person
found 18 hours ago
Beautiful property, relaxing landscape.
Reviewed on Jul 28, 2026
Top rated hotels for your The Berkshires vacation package
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
$128 nightly
The price is $143 total per night
$143 total
Aug 31 - Sep 1
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 aparthotel include a gym, free WiFi in public areas, and a business center.
Pool
Parking included
The Yankee Inn
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
17.41 mi from city center
$158 nightly
The price is $176 total per night
$176 total
Sep 14 - Sep 15
Total with taxes and fees
The Yankee Inn features an indoor pool, an outdoor pool, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area. Additional amenities include free WiFi in public areas, a hot tub, and a seasonal outdoor pool.
Pool
Hot Tub
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
17.93 mi from city center
$125 nightly
The price is $139 total per night
$139 total
Aug 31 - Sep 1
Total with taxes and fees
At Berkshire Mountain Lodge, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Other amenities at this golf aparthotel include a business center, an arcade/game room, and laundry facilities.
Pool
Hot Tub
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
