Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Quechee Inn at Marshland Farm
Price was $495, price is now $447 per person
$447
per person
Apr 24 - Apr 26
found 2 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 Wilderness Trails and Vermont Institiute of Natural Science are located nearby.
North Star Lodge and Resort
Price was $538, price is now $482 per person
$482
per person
Apr 24 - Apr 26
found 2 hours ago
Roundtrip flight included
New York (NYC) 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 Killington School for Tennis are located nearby.
Best Western Inn & Suites Rutland-Killington
Price was $522, price is now $472 per person
$472
per person
Apr 24 - Apr 26
found 2 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Stay at this hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Rock Climbing Center and Hathaway Farm are located nearby.
Days Inn by Wyndham Rutland/Killington Area
Price was $908, price is now $822 per person
$822
per person
May 5 - May 11
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Castle Hill Resort And Spa
Price was $1,268, price is now $1,171 per person
$1,171
per person
May 5 - May 11
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Lake Bomoseen Lodge
Price was $863, price is now $807 per person
$807
per person
Jun 5 - Jun 7
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Emrose Luxury Cabins
Price was $492, price is now $462 per person
$462
per person
Apr 24 - Apr 26
found 2 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Stay at this hotel in Brandon. Enjoy free WiFi, free parking, and 8 hot tubs. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.
The Mountain Inn at Killington
Price was $945, price is now $888 per person
$888
per person
May 5 - May 11
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
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.
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
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