Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Saratoga Casino Hotel
Price was $552, price is now $438 per person
$438
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Racetrack and Saratoga Performing Arts Center are located nearby.
Very nice rooms and clean. I'm not a casino person, but found it very comfortable and convenient. No food after 9 pm on a weekday. Suggest keep kitchen open, people might gamble and use facilities. Wanted food after 9, but nothing on premises when it's a casino open until 4 am. Foodwise do better. Rooms are great.
Reviewed on Oct 22, 2026
The Perch Hotel
Save 100% on your flight
Price was $1,522, price is now $1,022 per person
$1,022
per person
Dec 17 - Dec 20
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
South Shire
Price was $1,507, price is now $1,133 per person
$1,133
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.
Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants.
Reviewed on Oct 21, 2026
Hotel Kinsley
Price was $853, price is now $679 per person
$679
per person
Jan 4 - Jan 8
found 23 hours ago
Roundtrip 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 helpful staff and the clean rooms in our reviews. Popular attractions Birch Body Care and Volunteer Fireman's Hall and Museum of Kingston are located nearby.
Despite saying there was complimentary coffee in the rooms, there was no coffee machines or anything to make coffee in the rooms. The kitchen was several blocks away too.
Reviewed on Oct 21, 2026
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
Price was $1,112, price is now $905 per person
$905
per person
Jan 4 - Jan 8
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this cottage in Stone Ridge. Enjoy free parking, patios, and in-room fireplaces. Popular attractions Tongore Park Beach and Century House Historical Society are located nearby.
Wonderful
Reviewed on Mar 29, 2026
The Old Catskill Game Farm Inn
Save 100% on your flight
Price was $3,643, price is now $2,964 per person
$2,964
per person
Dec 17 - Dec 20
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Book a stay at this historic guesthouse in Catskill. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Kaaterskill Falls and North-South Lake Campground & Day Use Area are located nearby.
Everything was amazing. Shawn was awesome. He greeted you when we came in. It's definitely experiences. All I can say we had a great time. A little quirky.Amazing history set on 200 acres closed down zoo
Reviewed on Sep 21, 2026
The Hideout Catskills Cottage
Save 100% on your flight
Price was $1,896, price is now $1,544 per person
$1,544
per person
Nov 24 - Dec 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this vacation home in Kingston. Enjoy free parking and a garden. Popular attractions Rosendale Trestle and Rosendale Public Library are located nearby.
Country Inn & Suites by Radisson, Downtown Albany New York
Price was $857, price is now $701 per person
$701
per person
Dec 26 - Jan 2
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Popular attractions MVP Arena and Colonie Center Mall are located nearby.
Pittsfield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Pittsfield Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Jan 14 - Tue, Jan 19
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$273 Roundtrip, found 12 hours ago
$273
Roundtrip
found 12 hours ago
Thu, Jan 14 - Tue, Jan 19
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$293 Roundtrip, found 12 hours ago
$293
Roundtrip
found 12 hours ago
Thu, Jan 14 - Tue, Jan 19
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$293 Roundtrip, found 12 hours ago
$293
Roundtrip
found 12 hours ago
Sat, Oct 24 - Wed, Oct 28
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$336 Roundtrip, found 11 hours ago
$336
Roundtrip
found 11 hours ago
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