Pittsfield Vacations

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Top Hotel Deals

The Mountain Inn at Killington

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. ...
Woodstock Inn & Resort

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. ...
Killington Mountain Lodge, Tapestry Collection by Hilton

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 ...
The Jackson

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 ...
Emrose Luxury Cabins

Emrose Luxury Cabins

1246 Franklin Street Brandon VT
20.7 km from city center
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

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 ...
Mountain Meadows Lodge

Mountain Meadows Lodge

285 Thundering Brook Road Killington VT
11.27 km from city center
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 ...
Mountain Sports Inn

Mountain Sports Inn

813 Killington Road Killington VT
12.68 km from city center
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 ...
The Shire Woodstock

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

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 breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Brandon Inn

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 ...
Comfort Inn Rutland - Killington

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 ...
North Star Lodge and Resort

North Star Lodge and Resort

78 Weathervane Dr Killington VT
12.99 km from city center
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 ...
Days Inn by Wyndham Rutland/Killington Area

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 ...
Courtyard Middlebury

Courtyard Middlebury

309 Court Street Middlebury VT
37.43 km from city center
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 ...
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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.

American Airlines
Fri, Feb 19 - Mon, Mar 8
FLL
Fort Lauderdale - Hollywood Intl.
RUT
Rutland Southern Vermont Regional
$664
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Feb 19 from Fort Lauderdale - Hollywood Intl. to Rutland Southern Vermont Regional, returning Mon, Mar 8, priced at $664 found 5 days ago
United
Mon, Feb 1 - Sun, Feb 21
FLL
Fort Lauderdale - Hollywood Intl.
RUT
Rutland Southern Vermont Regional
$667
Roundtrip
found 6 days ago
Select United flight, departing Mon, Feb 1 from Fort Lauderdale - Hollywood Intl. to Rutland Southern Vermont Regional, returning Sun, Feb 21, priced at $667 found 6 days ago
Delta
Mon, Feb 1 - Sun, Feb 21
FLL
Fort Lauderdale - Hollywood Intl.
RUT
Rutland Southern Vermont Regional
$684
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Feb 1 from Fort Lauderdale - Hollywood Intl. to Rutland Southern Vermont Regional, returning Sun, Feb 21, priced at $684 found 6 days ago
JetBlue Airways
Mon, Feb 1 - Sun, Feb 21
FLL
Fort Lauderdale - Hollywood Intl.
RUT
Rutland Southern Vermont Regional
$724
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Feb 1 from Fort Lauderdale - Hollywood Intl. to Rutland Southern Vermont Regional, returning Sun, Feb 21, priced at $724 found 6 days ago