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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.
TownePlace Suites by Marriott Albany Downtown/Medical Center

TownePlace Suites by Marriott Albany Downtown/Medical Center

3 out of 5
Price was $533, price is now $444 per person
$444
per person
Dec 27 - Dec 31
found 24 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions MVP Arena and Colonie Center Mall are located nearby.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $1,044, price is now $816 per person
$816
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star guesthouse in Kingston. Enjoy free WiFi, free parking, and Netflix. Popular attractions Senate House State Historic Site and Volunteer Fireman's Hall and Museum of Kingston are located nearby.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Price was $787, price is now $658 per person
$658
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this 4-star 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.
Eastwind Oliverea Valley

Eastwind Oliverea Valley

2 out of 5
Price was $1,434, price is now $1,205 per person
$1,205
per person
Dec 19 - Dec 24
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Big Indian. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Catskill State Park and Belleayre Beach are located nearby.
Hampton Inn Kingston

Hampton Inn Kingston

2.5 out of 5
Price was $756, price is now $642 per person
$642
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hudson Valley Mall and Robert E. Post Memorial Park are located nearby.
Howard Hotel

Howard Hotel

2 out of 5
Price was $1,007, price is now $863 per person
$863
per person
Dec 19 - Dec 24
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Hudson. Enjoy free WiFi, a hair salon, and hydromassage showerheads. Popular attractions Hudson Opera House and Max and Lillian Katzman Theater are located nearby.
Hasbrouck House

Hasbrouck House

4 out of 5
Price was $1,734, price is now $1,506 per person
$1,506
per person
Dec 19 - Dec 24
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 4-star business-friendly hotel in Stone Ridge. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mohonk Lake and Tongore Park Beach are located nearby.
Sunshine Inn

Sunshine Inn

2 out of 5
Price was $870, price is now $759 per person
$759
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this hotel in Greenwich. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Greenwich Town Bathing Beach and Ashville Game Farm and Exotic Zoo are located nearby.
La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
Price was $938, price is now $823 per person
$823
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Colonie Center Mall and Curtain Call Theater are located nearby.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,034, price is now $757 per person
$757
per person
Dec 27 - Dec 31
found 24 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
TownePlace Suites Latham Albany Airport

TownePlace Suites Latham Albany Airport

3 out of 5
Price was $575, price is now $471 per person
$471
per person
Dec 27 - Dec 31
found 24 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Home2 Suites by Hilton Albany Wolf Rd

Home2 Suites by Hilton Albany Wolf Rd

3 out of 5
Price was $615, price is now $518 per person
$518
per person
Dec 27 - Dec 31
found 24 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

3-4 Night Vacations in Jacob's Pillow

Price found within the past 48 hours. Click for updated prices.
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $835, price is now $653 per person
$653
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Roundout
Price was $3,472, price is now $2,708 per person
$2,708
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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 $787, price is now $658 per person
$658
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,034, price is now $757 per person
$757
per person
Dec 27 - Dec 31
found 24 hours ago
Roundtrip non-stop 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.
Hampton Inn Kingston

Hampton Inn Kingston

2.5 out of 5
Price was $756, price is now $642 per person
$642
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $1,044, price is now $816 per person
$816
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Eastwind Oliverea Valley

Eastwind Oliverea Valley

2 out of 5
Price was $1,434, price is now $1,205 per person
$1,205
per person
Dec 19 - Dec 24
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Howard Hotel

Howard Hotel

2 out of 5
Price was $1,007, price is now $863 per person
$863
per person
Dec 19 - Dec 24
found 6 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
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, 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
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!
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.