Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Cortina Inn
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Stay at this 3-star business-friendly hotel in Rutland. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Green Mountain Shopping Plaza and Diamond Run Mall are located nearby.

Chateau Rooms
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Stay at this 4.5-star luxury guesthouse in Bolton Landing. Enjoy free WiFi, a full-service spa, and room service. Popular attractions Lake George and Adirondack Extreme Adventure Course are located nearby.

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Stay at this 3-star golf castle in Bolton Landing. Enjoy free WiFi, free parking, and furnished balconies or patios. Popular attractions Veterans Memorial Park Beach and Adirondack Extreme Adventure Course are located nearby.

Days Inn by Wyndham Rutland/Killington Area
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.

Silver Bay YMCA Inn and Conference Center
per person
Jul 17 - Jul 20
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Stay at this 3-star beach hotel in Silver Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Lake George and Huletts Landing Marina are located nearby.

The Mountain Inn at Killington
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.

North Star Lodge and Resort
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Fire Tower are located nearby.

The Waffelhaus In Killington 4 Bedroom Home
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Rutland (RUT)
Stay at this 3-star golf vacation home in Killington. Enjoy free WiFi, free parking, and cable/satellite TV service. Popular attractions Killington Resort and Fire Tower are located nearby.
Pittsfield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



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