Pittsfield Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Pittsfield Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Putney Inn
Price was $693, price is now $599 per person
$599
per person
Aug 15 - Aug 20
found 21 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) to Rutland (RUT)
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yellow Barn and Next Stage Arts are located nearby.
Days Inn by Wyndham Rutland/Killington Area
Price was $806, price is now $670 per person
$670
per person
Aug 15 - Aug 20
found 21 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) 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.
The Mountain Inn at Killington
Price was $790, price is now $660 per person
$660
per person
Aug 15 - Aug 20
found 21 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) 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 $855, price is now $729 per person
$729
per person
Aug 15 - Aug 20
found 21 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) 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.
Emrose Luxury Cabins
Price was $992, price is now $876 per person
$876
per person
Aug 15 - Aug 20
found 21 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) 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.
Comfort Inn Rutland - Killington
Price was $758, price is now $670 per person
$670
per person
Aug 15 - Aug 20
found 21 hours ago
Roundtrip non-stop flight included
Greensboro (GSO) 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 breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
Top Hotel Deals
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
15.28 km from city center
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
23.23 km from city center
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 ...
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
28.87 km from city center
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
15.82 km from city center
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. ...
My Place Hotel-Randolph VT
2440 Vermont 66 Randolph Center VT
24.72 km from city center
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 ...
The Shire Woodstock
46 Pleasant St. Woodstock VT
29.15 km from city center
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. ...
On The River Inn
1653 West Woodstock Road Woodstock VT
27.85 km from city center
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Hampton Inn Rutland
47 Farrell Rd Rutland VT
24.45 km from city center
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 ...
Brandon Inn
20 Park Street Brandon VT
22.21 km from city center
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 ...
Days Inn by Wyndham Rutland/Killington Area
401 US-7 Rutland VT
24.29 km from city center
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 ...
The Jackson
43 Senior Lane Woodstock VT
27.7 km from city center
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 ...
Lincoln Inn & Gallery
2709 West Woodstock Rd Woodstock VT
27.47 km from city center
Stay at this inn in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee ...
Sleep Woodstock Motel
4324 West Woodstock Road Woodstock VT
25.95 km from city center
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Aug 4 - Wed, Aug 12
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$370 Roundtrip, found 20 hours ago
$370
Roundtrip
found 20 hours ago
Tue, Aug 4 - Wed, Aug 12
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$390 Roundtrip, found 1 day ago
$390
Roundtrip
found 1 day ago
Tue, Jun 23 - Wed, Jul 8
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$455 Roundtrip, found 1 day ago
$455
Roundtrip
found 1 day ago
Tue, Jun 23 - Wed, Jul 8
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$480 Roundtrip, found 1 day ago
$480
Roundtrip
found 1 day ago