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Check prices for these dates

Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar
In one month
20 Mar - 22 Mar
In two months
17 Apr - 19 Apr

Our top choices for Pittsfield motels

Lobby

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (391 reviews)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is SAR 408
SAR 449 total
includes taxes & fees
18 Feb - 19 Feb
Middlebury Sweets Motel
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (557 reviews)
"So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. "
United States
JILL
Sleep Woodstock 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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"This My Place Hotel is in a great location. At this time of year it features an economical price. The room is super clean and accommodating. I highly recommend it. "
charlie 2-night trip
Posted 21 hours ago
My Place Hotel-Randolph VT

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 42 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. Rodeway Inn Rutland - Killington: 13.3 mi (21.5 km) from the heart of Pittsfield. Enjoy access to the 24-hour front desk, and freebies including breakfast, WiFi, and parking.
What can I do in Pittsfield?
Some outdoorsy places nearby include Green Mountain National Forest, Pico Peak, and Lakota Lake. You'll find these family-friendly sights in the area: Killington Adventure Center, Hathaway Farm, and Green Mountain Rock Climbing Center. Other places worth a visit include Pittsfield Town Hall and Roger Clark Memorial Central Library.
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.