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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.
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Price was $437, price is now $355 per person
$355
per person
Jul 14 - Jul 16
found 17 hours 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 Schenectady Light Opera Performing Arts Center are located nearby.
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,143, price is now $823 per person
$823
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $1,712, price is now $1,239 per person
$1,239
per person
Jun 19 - Jun 22
found 24 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Million Dollar Beach and Hearthstone Point Campground are located nearby.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,020, price is now $804 per person
$804
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and National Shrine of the Divine Mercy are located nearby.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $828, price is now $653 per person
$653
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
New York (NYC) 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 Tanglewood Music Center and National Shrine of the Divine Mercy are located nearby.
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 $1,193, price is now $959 per person
$959
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Book a stay at this 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 National Shrine of the Divine Mercy and Tanglewood Music Center are located nearby.
Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

3 out of 5
Price was $6,267, price is now $5,048 per person
$5,048
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this cottage in Stephentown. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Zema's Nursery and Alpine Super Slide are located nearby.
The Lake George Inn

The Lake George Inn

2 out of 5
Price was $731, price is now $590 per person
$590
per person
Jun 19 - Jun 22
found 24 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Million Dollar Beach and Six Flags Great Escape are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

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
Price was $898, price is now $652 per person
$652
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $1,712, price is now $1,239 per person
$1,239
per person
Jun 19 - Jun 22
found 24 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,020, price is now $804 per person
$804
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $828, price is now $653 per person
$653
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)

Pittsfield Vacation Packages 5-7 Night Stays

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
Price was $1,193, price is now $959 per person
$959
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Hotel On North

Hotel On North

3.5 out of 5
Price was $1,401, price is now $1,229 per person
$1,229
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
The Whitlock

The Whitlock

2 out of 5
Price was $1,391, price is now $1,223 per person
$1,223
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was $1,102, price is now $969 per person
$969
per person
Jun 15 - Jun 22
just found
Roundtrip flight included
Orlando (MCO) to Albany (ALB)

Top Flight Deals

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

Breeze Airways
Sat, May 23 - Wed, Jun 10
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$169 Roundtrip, just found
$169
Roundtrip
just found
Select Breeze Airways flight, departing Sat, May 23 from Southwest Florida Intl. to Albany Intl., returning Wed, Jun 10, priced at $169 just found
Delta
Sun, May 24 - Tue, Jun 9
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$393 Roundtrip, found 5 days ago
$393
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, May 24 from Southwest Florida Intl. to Albany Intl., returning Tue, Jun 9, priced at $393 found 5 days ago
American Airlines
Fri, May 22 - Sun, May 24
JFK
John F. Kennedy Intl.
ALB
Albany Intl.
$444 Roundtrip, found 6 days ago
$444
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 22 from John F. Kennedy Intl. to Albany Intl., returning Sun, May 24, priced at $444 found 6 days ago
United
Sat, May 23 - Wed, Jun 10
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$674 Roundtrip, just found
$674
Roundtrip
just found
Select United flight, departing Sat, May 23 from Southwest Florida Intl. to Albany Intl., returning Wed, Jun 10, priced at $674 just found