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Pittsfield Vacation Packages

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Pittsfield Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
Price was $371, price is now $307 per person
$307
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $550, price is now $418 per person
$418
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,544, price is now $1,227 per person
$1,227
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Book a stay at this golf hotel in Wilmington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and North Branch Deerfield River are located nearby.
Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,989, price is now $1,607 per person
$1,607
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this 3.5-star golf hotel in Manchester. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Museum of Creative Process and Hildene are located nearby.
The White House Inn

The White House Inn

3.5 out of 5
Price was $1,188, price is now $962 per person
$962
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this 3.5-star 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.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $1,733, price is now $1,406 per person
$1,406
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
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 $511, price is now $421 per person
$421
per person
Jan 7 - Jan 12
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star 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.
Four Points by Sheraton Albany

Four Points by Sheraton Albany

3 out of 5
Price was $428, price is now $356 per person
$356
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Albany. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions MVP Arena and Crossgates Mall are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
Price was $371, price is now $307 per person
$307
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $550, price is now $418 per person
$418
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The White House Inn

The White House Inn

3.5 out of 5
Price was $510, price is now $415 per person
$415
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Four Points by Sheraton Albany

Four Points by Sheraton Albany

3 out of 5
Price was $428, price is now $356 per person
$356
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)

Pittsfield Vacation Packages 5-7 Night Stays

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 $1,188, price is now $962 per person
$962
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,544, price is now $1,227 per person
$1,227
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,989, price is now $1,607 per person
$1,607
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $1,733, price is now $1,406 per person
$1,406
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Sat, Dec 6 - Mon, Dec 15
JFK
John F. Kennedy Intl.
ALB
Albany Intl.
$284 Roundtrip, found 5 days ago
$284
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Dec 6 from John F. Kennedy Intl. to Albany Intl., returning Mon, Dec 15, priced at $284 found 5 days ago
American Airlines
Sat, Dec 6 - Mon, Dec 15
JFK
John F. Kennedy Intl.
ALB
Albany Intl.
$300 Roundtrip, found 5 days ago
$300
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Dec 6 from John F. Kennedy Intl. to Albany Intl., returning Mon, Dec 15, priced at $300 found 5 days ago
Delta
Sat, Dec 6 - Mon, Dec 15
JFK
John F. Kennedy Intl.
ALB
Albany Intl.
$331 Roundtrip, found 5 days ago
$331
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Dec 6 from John F. Kennedy Intl. to Albany Intl., returning Mon, Dec 15, priced at $331 found 5 days ago
Breeze Airways
Sat, Dec 27 - Sat, Jan 3
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$341 Roundtrip, found 3 days ago
$341
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Dec 27 from Southwest Florida Intl. to Albany Intl., returning Sat, Jan 3, priced at $341 found 3 days ago