Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast
Price was $678, price is now $572 per person
$572
per person
Jul 6 - Jul 10
found 24 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
The Quechee Inn at Marshland Farm
Price was $768, price is now $610 per person
$610
per person
Jul 6 - Jul 10
found 24 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this golf hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Quechee Gorge Bridge and Wilderness Trails are located nearby.
Lake Bomoseen Lodge
Price was $882, price is now $721 per person
$721
per person
Jul 6 - Jul 10
found 24 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
Chateau Rooms
Price was $1,151, price is now $941 per person
$941
per person
Jul 17 - Jul 19
found 11 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this 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.
The Mountain Inn at Killington
Price was $726, price is now $625 per person
$625
per person
Jul 6 - Jul 10
found 24 hours ago
Roundtrip flight included
New York (NYC) 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.
The Vermont Inn
Price was $718, price is now $637 per person
$637
per person
Jul 6 - Jul 10
found 24 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Killington Resort and Golden Express Quad are located nearby.
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Save 100% on your flight
Price was $3,367, price is now $3,000 per person
$3,000
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this 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.
Silver Bay YMCA Inn and Conference Center
Price was $836, price is now $763 per person
$763
per person
Jul 17 - Jul 19
found 11 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this 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.
Pittsfield Vacation Packages 3-4 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.
Mon, Jun 1 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$134 Roundtrip, found 6 hours ago
$134
Roundtrip
found 6 hours ago
Sun, May 31 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 3 hours ago
$184
Roundtrip
found 3 hours ago
Tue, Oct 13 - Tue, Oct 20
BWI
Baltimore Washington Intl. Thurgood Marshall
RUT
Rutland Southern Vermont Regional
$354 Roundtrip, found 20 hours ago
$354
Roundtrip
found 20 hours ago
Wed, Jun 3 - Wed, Jun 3
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$481 Roundtrip, found 7 hours ago
$481
Roundtrip
found 7 hours ago
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