A lake surrounded by autumn-colored trees and a rocky shoreline.

Search Motels in Pittsfield from CA $140

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Pittsfield motels

Deluxe Suite | Private kitchen

1. Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (599 reviews)
"Wonderful little place to stay. Very quiet, very safe, and one of the cleanest roadside hotels I've stayed at in a long time."
United States
Sean
The price is CA $127
CA $140 total
includes taxes & fees
Aug 31 - Sep 1
Sleep Woodstock Motel
Lobby

2. Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (404 reviews)
"Lovely staff, a clean and comfortable room with a candy theme, a nice shower, an amazing candy and chocolate shop! We have stayed here several times over the last few years and we always love it!"
United States
Emily
The price is CA $215
CA $236 total
includes taxes & fees
Aug 9 - Aug 10
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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Amazing! Will visit again."
Leah 4-night trip
Posted 10 hours ago
Woodstock Inn & Resort

Find out more about Pittsfield

Pittsfield Motels information

Number of reviews
1,003
Accommodation
8 Motels
Lowest Price
CA $140
Highest Price
CA $236

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. 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 Silver Lake State Park. You'll find these family-friendly sights in the area: Killington Adventure Center, Hathaway Farm, 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.

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