Pittsfield Vacations
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Pittsfield Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Greenbrier Inn
$1,259
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Gifford Woods State Park are located nearby.
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on Aug 3, 2026
Mountain Green Resort
$2,245
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Black Dog Sports are located nearby.
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
$1,274
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus.
Reviewed on Aug 22, 2026
The Suites at Killington Center
$1,369
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
The Mountain Inn at Killington
$1,268
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Columbia (CAE) 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.
Such a great experience and stay. We checked in as guests and left as family. The rooms were clean and comfortable, the location perfect, and the staff beyond friendly and helpful. Will definitely be returning.
Reviewed on Aug 25, 2026
North Star Lodge and Resort
$1,387
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Columbia (CAE) 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.
Top Hotel Deals
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
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. ...
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Book a stay at this golf hotel in Killington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Emrose Luxury Cabins
1246 Franklin Street Brandon VT
Book a stay at this family-friendly hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Stephen A Douglas Birthplace and ...
My Place Hotel-Randolph VT
2440 Vermont 66 Randolph Center VT
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture ...
On The River Inn
1653 West Woodstock Road Woodstock VT
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Courtyard Middlebury
309 Court Street Middlebury VT
Book a stay at this business-friendly hotel in Middlebury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
The Shire Woodstock
46 Pleasant St. Woodstock VT
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Jackson
43 Senior Lane Woodstock VT
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions ...
Mountain Meadows Lodge
285 Thundering Brook Road Killington VT
Book a stay at this family-friendly hotel in Killington. Enjoy free breakfast, a sauna, and a 24-hour front desk. Our guests praise the helpful staff in our ...
Brandon Inn
20 Park Street Brandon VT
Stay at this hotel in Brandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Mountain Sports Inn
813 Killington Road Killington VT
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Days Inn by Wyndham Rutland/Killington Area
401 US-7 Rutland VT
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 ...
Sleep Woodstock Motel
4324 West Woodstock Road Woodstock VT
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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