Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Yankee Inn
Price was $615, price is now $548 per person
$548
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Breakfast was h asic everything else was perfect
Reviewed on Nov 12, 2026
Brook Bound Inn
Price was $1,075, price is now $807 per person
$807
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
The place was clean and beautiful. You need to check with Expedia . I didn’t get the steps to get in, since there is nobody on site. to check in. I call the phone on site. Somebody call me back and walk me through step to get in.
Reviewed on Oct 19, 2026
The White House Inn
Price was $823, price is now $711 per person
$711
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. 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.
—-
Reviewed on Nov 11, 2026
The Equinox Golf Resort And Spa
Price was $762, price is now $665 per person
$665
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Very unique property with a feel like home feel
Good breakfast
.
Reviewed on Nov 10, 2026
La Quinta Inn & Suites by Wyndham Latham Albany Airport
Price was $786, price is now $688 per person
$688
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this 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.
Clean, comfortable room at a good price. Microwave in the room, small shop downstairs for food items. Above average breakfast offerings.
Reviewed on Nov 12, 2026
Hotel Vervana, Trademark Collection by Wyndham
Price was $624, price is now $549 per person
$549
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this ski hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bennington Museum and Fiddlehead at Four Corners are located nearby.
staff was very helpful. room was good and comfortable.
ice machine was in another building , but not too inconvenient.
waffle machine was broken, a bit disappointing. but not horrible.
Reviewed on Nov 12, 2026
Hyatt House Schenectady / Mohawk Harbor
Price was $755, price is now $665 per person
$665
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this hotel in Schenectady. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Rivers Casino & Resort and Schenectady City Hall are located nearby.
The Four Chimneys Inn
Price was $887, price is now $795 per person
$795
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this golf B&B in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Old First Congregational Church and Bennington Museum are located nearby.
Very nice, quiet place. Relaxing and cute.
Reviewed on Sep 7, 2026
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.
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Wed, Dec 23 - Tue, Jan 5
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$361 Roundtrip, found 4 days ago
$361
Roundtrip
found 4 days ago
Sat, Dec 26 - Fri, Jan 8
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$403 Roundtrip, found 4 days ago
$403
Roundtrip
found 4 days ago
Sun, Nov 22 - Wed, Dec 2
JFK
John F. Kennedy Intl.
ALB
Albany Intl.
$490 Roundtrip, found 6 days ago
$490
Roundtrip
found 6 days ago
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