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Jacob'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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
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 Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
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

Club Wyndham Bentley Brook

3 out of 5
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

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
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

Berkshire Mountain Lodge

3 out of 5
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

The Dewey

3.5 out of 5
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

Super 8 by Wyndham Albany

2 out of 5
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

Super 8 by Wyndham Schenectady/Albany Area

2 out of 5
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

Vacation Village in the Berkshires

3 out of 5
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

Berkshires Untold

3.5 out of 5
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

The Whitlock

2 out of 5
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.
Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
per person
Sep 8 - Sep 12
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Hasbrouck House

Hasbrouck House

4 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)

5-7 Night Vacations in Jacob's Pillow

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Schenectady/Albany Area

Super 8 by Wyndham Schenectady/Albany Area

2 out of 5
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Super 8 by Wyndham Albany

Super 8 by Wyndham Albany

2 out of 5
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)

Jacob's Pillow Last Minute Hotel Deals

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

3 out of 5
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.
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
A-frame Cabin w/ Furnished Deck in Becket!

A-frame Cabin w/ Furnished Deck in Becket!

3 out of 5
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 ...
A-frame Cabin w/ Furnished Deck in Becket!
Berkshires Cabin 2 Mi to Appalachian Trail!

Berkshires Cabin 2 Mi to Appalachian Trail!

3 out of 5
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 ...
Berkshires Cabin 2 Mi to Appalachian Trail!
Cozy Becket Cottage Escape w/ Lake Access!

Cozy Becket Cottage Escape w/ Lake Access!

3 out of 5
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 ...
Cozy Becket Cottage Escape w/ Lake Access!
Becket Home w/ 3-season Porch: Walk to Lake Access

Becket Home w/ 3-season Porch: Walk to Lake Access

3 out of 5
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 Home w/ 3-season Porch: Walk to Lake Access
Becket Motel

Becket Motel

2.5 out of 5
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 ...
Becket Motel
See all 508 properties in Jacob's Pillow
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.