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Check prices for these dates

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21 Nov - 23 Nov
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28 Nov - 30 Nov
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12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

Motels in Pittsfield

Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout drapes
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (541)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is AED 304
AED 496 total
includes taxes & fees
16 Nov - 17 Nov
Sleep Woodstock Motel
Classic Room, 2 Queen Beds | Desk, iron/ironing board, free WiFi, bed sheets
Middlebury Sweets Motel

Middlebury Sweets Motel

2.5 star property
Middlebury
8.6 out of 10, Excellent, (387)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is AED 400
AED 440 total
includes taxes & fees
19 Nov - 20 Nov
Middlebury Sweets Motel
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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Top Pittsfield Hotel Reviews

The Jackson

The Jackson

10/10 Excellent
"The room, the staff, the amenities were what we were hoping for. The Jackson is a great place to stay! "
Frederick 2-night trip
Posted 18 hours ago
The Jackson

Frequently asked questions

What can I expect from a motel trip to Pittsfield?
If you're having a hard time finding motels in Pittsfield, expand your search to find motels in the surrounding area or let us help you find a similar property from more than 40 hotels and other lodging options. Simply use our search tools to filter by price per night or cost-saving amenities such as free parking and free airport transportation.
What are motels like?
At most motels, you'll often find an outdoor pool and free parking. When you stay at a motel, you'll usually access your room from an outside corridor overlooking the parking lot. In the U.S., motels became more commonplace at the end of the 1940s with the appeal of road trip vacations, peaking in the mid-1960s with more than 60,000 properties.
What are the best motels in Pittsfield?
Here you'll find some of Expedia customers' favorite motels in the larger area. Sleep Woodstock Motel is located 16.1 mi (26 km) from the heart of Pittsfield. Enjoy access to the picnic area, and freebies including WiFi and parking. Middlebury Sweets Motel: Free WiFi and free parking are available during your stay, along with room amenities like a private yard. Central Pittsfield is 22.2 mi (35.8 km) away. Happy Bear Motel: Enjoy access to the free WiFi and free parking, as well as room amenities like a microwave. Located 8.7 mi (14 km) from the heart of Pittsfield. Econo Lodge Rutland City near Hwy 7: Central Pittsfield is 14.7 mi (23.6 km) away. A business center along with freebies like breakfast, WiFi, and parking are available during your stay. Travel Inn: 13.2 mi (21.2 km) from the heart of Pittsfield. Enjoy access to the laundry facilities, and freebies including WiFi and parking.
What can I do in Pittsfield?
Some outdoorsy places nearby include Green Mountain National Forest, Pico Peak, and Silver Lake State Park. You'll find these family-friendly sights in the area: Killington Adventure Center, Green Mountain Rock Climbing Center, and Black Dog Sports. Other places worth a visit include Roger Clark Memorial Central Library and Pittsfield Town Hall.
What's the seasonal weather like in Pittsfield?
Weather can make or break a roadtrip, so we've gathered some data about year-round temperatures in Pittsfield to help you plan yours. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.
What are my options for getting around Pittsfield when staying in a motel?
We've gathered some information about getting around Pittsfield to help you navigate your stay: Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the city center. Otherwise, you can search for flights to Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you'd like to explore around the area, you may want a rental car for your journey.