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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.
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
Price was $520, price is now $430 per person
$430
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Book a stay at this business-friendly hotel in Clifton Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Regal Clifton Park and Clifton Common are located nearby.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $976, price is now $708 per person
$708
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 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 The Bookstore and Lenox Library are located nearby.
The White House Inn

The White House Inn

3.5 out of 5
Price was $863, price is now $666 per person
$666
per person
Dec 28 - Jan 2
found 16 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
Bluebird Spa City Motor Lodge

Bluebird Spa City Motor Lodge

3 out of 5
Price was $893, price is now $708 per person
$708
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $794, price is now $629 per person
$629
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this 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.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Price was $709, price is now $578 per person
$578
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Scene One Movieland are located nearby.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,026 per person
$1,026
per person
Dec 28 - Jan 2
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $1,303, price is now $824 per person
$824
per person
Dec 28 - Jan 2
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesterwood and Norman Rockwell Museum are located nearby.
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $1,141, price is now $769 per person
$769
per person
Dec 28 - Jan 2
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard Corner are located nearby.
Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Save 100% on your flight
Price was $5,233, price is now $3,586 per person
$3,586
per person
Dec 28 - Jan 2
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this guesthouse in Kingston. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hudson River Maritime Museum and Trolley Museum of New York are located nearby.
Gedney Farm

Gedney Farm

3.5 out of 5
Save 100% on your flight
Price was $759, price is now $523 per person
$523
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are located nearby.
East Rock Inn

East Rock Inn

2 out of 5
Price was $710, price is now $544 per person
$544
per person
Dec 28 - Jan 2
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Popular attractions Housatonic River and Housatonic River Walk are located nearby.

3-4 Night Vacations in Jacob's Pillow

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $794, price is now $629 per person
$629
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $976, price is now $708 per person
$708
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $866, price is now $684 per person
$684
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
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
Price was $823, price is now $651 per person
$651
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)

5-7 Night Vacations in Jacob's Pillow

Price found within the past 48 hours. Click for updated prices.
The White House Inn

The White House Inn

3.5 out of 5
Price was $863, price is now $666 per person
$666
per person
Dec 28 - Jan 2
found 16 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $884, price is now $671 per person
$671
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,026 per person
$1,026
per person
Dec 28 - Jan 2
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $1,303, price is now $824 per person
$824
per person
Dec 28 - Jan 2
found 22 hours ago
Roundtrip flight included
Orlando (MCO) 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 MA
Stay at this 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 MA
Book a stay at this business-friendly cottage in Becket. Enjoy free parking, in-room fireplaces, and air conditioning. 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 MA
Stay at this cottage in Otis. Enjoy free parking and in-room fireplaces. Popular attractions Jacob's Pillow and McLennan Reservation are located nearby.
Berkshires Cabin 2 Mi to Appalachian Trail!
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 MA
Stay at this cottage in Becket. Enjoy free parking, balconies, and in-room fireplaces. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
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 505 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.