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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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

Sleep Woodstock Motel
Deluxe Suite | Individually decorated, desk, blackout drapes, iron/ironing board

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (475)
"Great motel that is much nicer than your typical motel"
The price is AED 375
AED 473 total
includes taxes & fees
30 Mar - 31 Mar
Sleep Woodstock Motel
Middlebury Sweets Motel
Classic Room, 2 Queen Beds | Desk, iron/ironing board, free WiFi, bed sheets

Middlebury Sweets Motel

2.5 star property
8.4 out of 10, Very Good, (349)
"Loved the candy store too !! The ladies were very friendly !!"
The price is AED 440
AED 484 total
includes taxes & fees
26 Mar - 27 Mar
Middlebury Sweets Motel
Happy Bear Motel
Exterior

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
Lobby

Econo Lodge Rutland City near Hwy 7

2.0 star property
5.4 out of 10, (121)
"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
Val Roc Inn
Property entrance

Val Roc Inn

2.0 star property
Val Roc Inn
Travel Inn
Room, 2 Double Beds | Free WiFi, bed sheets

Travel Inn

2.0 star property
5.4 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
The Cabins at Autumn Mountain Winery
Food and drink

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
Pool

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
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 Vermont Ski and Snowmobiling House
Interior

Killington Vermont Ski and Snowmobiling House

9.4 out of 10, Exceptional, (42)
"Good utilitarian property for fall leaf touring. Most everything worked ok, great for large family group but definitely not for someone desiring a fully furnished or decorated place. "
Killington Vermont Ski and Snowmobiling House
Killington area home - 4-seasons & hot tub. Sleeps 13+
Property grounds

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (116)
"We stayed at this property for a ski weekend in March. 8 guys fit comfortably and the accommodations were perfect. Property was as advertised and very clean. We enjoyed the hot tub after hitting the slopes which was a great way to finish the day. Owner was very accommodating and quick to reply to any inquiries or questions. 10/10"
Killington area home - 4-seasons & hot tub. Sleeps 13+
Private Killington Area Inn all to Yourself!
Fridge, microwave, oven, stovetop

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Eric is a perfect host! The inn is perfect, 9 rooms, private bathrooms. The kitchen is awesome, great appliances and big enough for everyone to be in the kitchen at the same time. This was our third year with family staying and celebrating. We will be back!"
Private Killington Area Inn all to Yourself!
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 41 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. Val Roc Inn: 11.8 mi (19 km) from the heart of Pittsfield. Enjoy access to the seasonal outdoor pool, and freebies including 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, 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.