Search Deals onJacob's Pillow Vacation Packages
Jacob's Pillow Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.


The Cornell Inn, Lenox & The Berkshires
per person
Sep 8 - Sep 12
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.

Club Wyndham Bentley Brook
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Hampton Inn & Suites Berkshires-Lenox
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

Berkshire Mountain Lodge
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.

The Dewey
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star guesthouse in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the breakfast in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.

Super 8 by Wyndham Albany
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

Super 8 by Wyndham Schenectady/Albany Area
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Rivers Casino & Resort and Rollarama Skating Center are located nearby.

Vacation Village in the Berkshires
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

Berkshires Untold
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.

The Whitlock
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and The Bookstore are located nearby.
3-4 Night Vacations in Jacob's Pillow
Price found within the past 48 hours. Click for updated prices.



5-7 Night Vacations in Jacob's Pillow
Price found within the past 48 hours. Click for updated prices.



Jacob's Pillow Last Minute Hotel Deals

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Becket
Stay at this 3-star cottage in Becket. Enjoy free parking, a garden, and patios. Popular attractions Jacob's Pillow and Pyramid Lake are located nearby.

A-frame Cabin w/ Furnished Deck in Becket!
Becket
Stay at this 3-star business-friendly cottage in Becket. Enjoy free parking, balconies, and in-room fireplaces. Popular attractions Pyramid Lake and Jacob's ...

Berkshires Cabin 2 Mi to Appalachian Trail!
Otis
Stay at this 3-star cottage in Otis. Enjoy free parking and in-room fireplaces. Popular attractions Jacob's Pillow and McLennan Reservation are located ...

Cozy Becket Cottage Escape w/ Lake Access!
Becket
Stay at this 3-star cottage in Becket. Enjoy free parking and an in-room coffeemaker. Popular attractions Pyramid Lake and Iroquis Waterfront are located ...

Becket Home w/ 3-season Porch: Walk to Lake Access
Becket
Stay at this 3-star cottage in Becket. Enjoy free parking, balconies, and in-room fireplaces. Popular attractions Pyramid Lake and Becket Land Trust Historic ...

Becket Motel
29 Chester Rd, Becket, MA
Stay at this motel in Becket. Enjoy free WiFi, free parking, and room service. Popular attractions Becket Land Trust Historic Quarry and Becket Quarry are located ...
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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Hotels Near Points of Interest in Jacob's Pillow
- Hotels near Tanglewood Music Center
- Hotels near National Shrine of the Divine Mercy
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- Hotels near The Mount
- Hotels near Lee Premium Outlets
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- Hotels near Naumkeag Museum
- Hotels near Berkshire Botanical Garden
- Hotels near Otis Reservoir
- Hotels near Housatonic River
- Hotels near Shakespeare and Company
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Car Rentals in Jacob's Pillow
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