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Compare 8 Motels in Pittsfield with updated reviews, rates, and availability.

Sleep Woodstock Motel
Exterior
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (399)
"Easy check in and out, nice clean room with good coffee maker and well set up fridge, towels, soaps, etc."
The price is SAR 1,096
SAR 1,205 total
includes taxes & fees
25 Sep - 26 Sep
Sleep Woodstock Motel
Middlebury Sweets Motel
Exterior
Middlebury Sweets Motel
2.5 star property
8.4 out of 10, Very Good, (321)
"Appreciated the clean room. The bathroom door needs to be adjusted to close."
The price is SAR 491
SAR 540 total
includes taxes & fees
23 Oct - 24 Oct
Middlebury Sweets Motel
Happy Bear Motel
Room
Happy Bear Motel
2.0 star property
7.0 out of 10, Good, (279)
"It was amazing. Clean room. Awesome hosts!"
Happy Bear Motel
Econo Lodge Rutland City near Hwy 7
Exterior
Econo Lodge Rutland City near Hwy 7
2.0 star property
5.4 out of 10, (120)
"Even though I was told I didn’t have a reservation, this got sorted out and the check in couldn’t have been friendlier. Nice booked breakfast given out since I was checking out before their breakfast time. "
Econo Lodge Rutland City near Hwy 7
Travel Inn
Property entrance
Travel Inn
2.0 star property
5.2 out of 10, (56)
"I called the hotel 2 weeks before to confirm my reservation to which I was told it's fine. Saturday evening before I left New York I called to remind them I'd be there late and to have the heat on in the room and I was told no problem. Later I received an voicemail stating that they had no room for me. The annoyance is that hotels.com has my confirmation for my reservation, So the communication is almost non-existent."
Travel Inn
Val Roc Inn
Property entrance
Val Roc Inn
2.0 star property
Val Roc Inn
The Cabins at Autumn Mountain Winery
Property grounds
The Cabins at Autumn Mountain Winery
2.0 star property
7.6 out of 10, Good, (90)
"This was on a family trip after burying our mother. We were the ONLY ones staying, yet they wouldn't give us the cabin with wi fi. The old lock locked us out late at night and it took 30 minutes for them to help us. When I complained, they kicked us out and called the police who had us drive away in the middle of the night with an 11 yr old. "
The Cabins at Autumn Mountain Winery
Rodeway Inn
Exterior
Rodeway Inn
2.0 star property
5.6 out of 10, (327)
"Very nice staff and the room was very comfortable and quiet. My only comment would be that the dingy shower walls could use a bit of scrubbing to make them gleam. icrowave and oven and coffee were a nice plus. "
Rodeway Inn
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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.
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Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 12+
Here's the main living area - dining is up on the left
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (111)
"We stayed for a small bachelor party and had a great time! Everyone had room and there was plenty to do."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (462)
"If you’re looking for rest and relaxation this is it. You are one with nature at this cabin which has everything you need. Host was very nice and accommodating. Plenty of yard games for the family and trails to explore. Hope to be back in the future. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (38)
"Absolutely perfect! Very nice location. Quiet and cozy little townhome. Short drive to Bear Mountain and Killington Ski Resort. Amazing area with plenty of awesome views."
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.

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 31 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 Pico Peak, Killington Peak, and Texas Falls Recreation Area. You’ll find these family-friendly sights in the area: Killington Adventure Center, Black Dog Sports, and Hathaway Farm. While you’re checking out the area, consider visiting Green Mountain National Golf Course, Pico Mountain at Killington Ski Resort, and Killington Golf Course.
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. Average annual precipitation for Pittsfield is 54 inches.
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.