Pittsfield Vacations
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Pittsfield Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area
per person
Oct 4 - Oct 10
found 19 hours ago
Roundtrip flight included
Madison (MSN) 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.
North Star Lodge and Resort
per person
Oct 4 - Oct 10
found 19 hours ago
Roundtrip flight included
Madison (MSN) 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 Fire Tower are located nearby.
The Mountain Inn at Killington
per person
Oct 4 - Oct 10
found 19 hours ago
Roundtrip flight included
Madison (MSN) 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.
Top Hotel Deals
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
28.87 km from city center
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
The Shire Woodstock
46 Pleasant St., Woodstock, VT
29.15 km from city center
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
Days Inn by Wyndham Rutland/Killington Area
401 US-7, Located At The Junction Of Us 4 And 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 ...
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 ...
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. ...
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 ...
Brandon Inn
20 Park Street, Brandon, VT
22.21 km from city center
Stay at this 3-star hotel in Brandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Cortina Inn
476 Holiday Drive, Rutland, VT
24.51 km from city center
Stay at this 3-star business-friendly hotel in Rutland. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Green Mountain Shopping ...
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd, Killington, VT
15.28 km from city center
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
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 Sports Inn
813 Killington Road, Killington, VT
12.71 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 ...
On The River Inn
1653 West Woodstock Road, Woodstock, VT
27.79 km from city center
Stay at this 4-star family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Lincoln Inn & Gallery
2709 West Woodstock Rd, Woodstock, VT
27.47 km from city center
Stay at this 3-star inn in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Union Arena Community Center and Ottaquechee River ...
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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