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

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Our top choices for Pittsfield hotels

Breakfast included
Hotel
Reserve now, pay later
Pet friendly
Wifi Included
Lobby sitting area
Premium Suite, Multiple Beds | Living area | 24-inch TV with cable channels
Lobby lounge
Deluxe Suite, 3 Bedrooms | Travel crib, rollaway beds (free), WiFi (free), individually decorated

1. Mountain Sports Inn

Mountain Sports Inn
Killington
United States
Davis
￥17,374
￥19,111 total
includes taxes & fees
Aug 17 - Aug 18
Mountain Sports Inn
Breakfast and dinner served
Outdoor pool, a heated pool
Reception
Superior Double Queen with Balcony | In-room safe, blackout drapes, WiFi (free), individually decorated

2. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
United States
Travis
￥19,939
￥23,032 total
includes taxes & fees
Aug 17 - Aug 18
The Mountain Inn at Killington
Interior detail
Lobby sitting area
Outdoor wedding area
Lobby sitting area

3. The Trailside Inn

The Trailside Inn
North Sherburne
United States
Niall
￥25,391
￥27,930 total
includes taxes & fees
Aug 31 - Sep 1
The Trailside Inn
Fireplace
Restaurant
Suite, 1 Bedroom | Private spa tub
Exterior

4. North Star Lodge and Resort

North Star Lodge and Resort
Killington
United States
Jessica
￥19,286
￥21,214 total
includes taxes & fees
Aug 16 - Aug 17
North Star Lodge and Resort
Lake view
Exterior
Lobby lounge
Lobby lounge

5. Mountain Meadows Lodge

Mountain Meadows Lodge
Killington
United States
Barry
￥25,746
￥32,307 total
includes taxes & fees
Sep 1 - Sep 2
Mountain Meadows Lodge
Lobby
Dinner served
Indoor pool
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

6. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
Rutland
United States
Darshil
￥19,533
￥21,486 total
includes taxes & fees
Aug 16 - Aug 17
Comfort Inn Rutland - Killington
Free daily buffet breakfast
Exterior
Suite, 1 King Bed, Jetted Tub | Living area | 32-inch LCD TV with cable channels, TV, pay movies
Exterior

7. Hampton Inn Rutland

Hampton Inn Rutland
Rutland
United States
Tarsha
￥20,792
￥22,870 total
includes taxes & fees
Aug 30 - Aug 31
Hampton Inn Rutland
Lobby
Suite, 2 Queen Beds, Non Smoking, Kitchen (Third bed is a Sofabed) | Blackout drapes, iron/ironing board, bed sheets
Exterior
Lobby

8. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
Rutland
United States
Alex
￥24,245
￥26,669 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Inn & Suites Rutland-Killington
Lounge
Snowshoeing
32-inch flat-screen TV with cable channels, TV
32-inch flat-screen TV with cable channels, TV

9. Greenbrier Inn

Greenbrier Inn
Killington
United States
David
￥26,873
￥30,970 total
includes taxes & fees
Aug 15 - Aug 16
Greenbrier Inn
BBQ/picnic area
Lobby sitting area
Front of property
Premium bedding, pillowtop beds, desk, blackout drapes

10. My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
Randolph Center
United States
Joey
￥21,690
￥23,642 total
includes taxes & fees
Sep 6 - Sep 7
My Place Hotel-Randolph VT
The Jewel | Living area | TV
The Jewel | Living room | TV
The Jewel | Laptop workspace, iron/ironing board, individually decorated
Campion | Living area | TV

11. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
United States
Kristen
￥51,802
￥56,464 total
includes taxes & fees
Sep 3 - Sep 4
The Mountain Top Inn & Resort
Lobby
Indoor pool
Free daily on-the-go breakfast
Reception

12. Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
Rutland
United States
Douglas
￥18,832
￥20,714 total
includes taxes & fees
Aug 23 - Aug 24
Days Inn by Wyndham Rutland/Killington Area
Front of property
Front of property
Exterior
Exterior

13. Brandon Inn

Brandon Inn
Brandon
Canada
Michael
￥22,954
￥25,249 total
includes taxes & fees
Aug 20 - Aug 21
Brandon Inn
Exterior
Lobby
Terrace/patio
Sports facility

14. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington
United States
Nicole
￥22,099
￥24,309 total
includes taxes & fees
Aug 30 - Aug 31
Killington Mountain Lodge, Tapestry Collection by Hilton
Exterior
Exterior
Premium Room, 2 Double Beds | Memory foam beds, desk, WiFi (free), bed sheets
Premium Room, 1 Queen Bed | Memory foam beds, desk, WiFi (free), bed sheets

15. Après Inn Killington

Après Inn Killington
Killington
United States
Lei
￥21,996
￥24,196 total
includes taxes & fees
Aug 31 - Sep 1
Après Inn Killington
Front of property
Dining room
Reception
Golf

16. Snowed Inn

Snowed Inn
Killington
United States
Greg
￥20,253
￥24,506 total
includes taxes & fees
Aug 17 - Aug 18
Snowed Inn
Elite Cabin, 1 King Bed, Sauna | Laptop workspace, blackout drapes, WiFi (free), individually decorated
Exterior
Fitness facility
Family Cabin, 2 Queen Beds | Room amenity

17. Emrose Luxury Cabins

Emrose Luxury Cabins
Brandon
United States
Mycheala
￥25,821
￥29,178 total
includes taxes & fees
Aug 18 - Aug 19
Emrose Luxury Cabins
House, 2 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, toaster
House, 2 Bedrooms | Interior
House, 2 Bedrooms | Terrace/patio
House, 2 Bedrooms | Interior

18. Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
North Sherburne
￥52,011
￥102,115 total
includes taxes & fees
Aug 18 - Aug 19
Killington A-frame 2 Bedroom Home
Deluxe Suite | Private kitchen | Coffee/tea maker, mini-fridge, microwave, freezer
Deluxe Suite | Desk, blackout drapes, iron/ironing board, WiFi (free)
Electric vehicle charging station
Exterior

19. Sleep Woodstock Motel

Sleep Woodstock Motel
Woodstock
United States
Sean
￥14,345
￥21,916 total
includes taxes & fees
Aug 19 - Aug 20
Sleep Woodstock Motel
Exterior
The Trillium Room | 1 bedroom, iron/ironing board, WiFi (free)
Exterior
Restaurant

20. Inn at Neshobe River

Inn at Neshobe River
Brandon
United States
Keith
￥27,893
￥30,682 total
includes taxes & fees
Aug 24 - Aug 25
Inn at Neshobe River
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Stay near popular Pittsfield attractions

Roger Clark Memorial Central Library

After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.
See properties

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
See properties

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

See all hotels in Pittsfield
A lake surrounded by autumn-colored trees and a rocky shoreline.

Top Pittsfield Hotel Reviews

Brandon Inn

Brandon Inn

10/10 Excellent
"I've been fortunate to have traveled here in the U.S. and abroad, many times. The Brandon Inn reminds me so much of hotels and inns I've stayed at throughout Europe....clean, accommodating and genuine. My wife and I have stayed here several times and we enjoy it - and the area - very much."
Mike 2-night trip
Posted 1 hour ago
Brandon Inn
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"We’ve stayed twice here and really enjoy it. The rooms have full size refrigerators and stove tops. The grills outside are well maintained."
Cherie 3-night trip
Posted 2 hours ago
My Place Hotel-Randolph VT
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Stay was great room was clean and staff was great also."
Al 2-night trip
Posted 20 hours ago
Days Inn by Wyndham Rutland/Killington Area
Mountain Sports Inn

Mountain Sports Inn

8/10 Good
"This is an older building, but clean and well maintained. The AC window units worked very well. The breakfast was tailored to meet our needs and excellent. The staff were friendly, caring and always available, even though summertime has fewer visitors than during the ski season. Highly recommend for the value!"
Neil 2-night trip
Posted 23 hours ago
Mountain Sports Inn
The Shire Woodstock

The Shire Woodstock

8/10 Good
"The staff was helpful. The room was clean. There was some 1st floor construction that it would have been nice to know about prior to check in. It didn’t impact our stay but made things a bit dusty. Very conveniently located to downtown area."
Theresa 1-night trip
Posted 1 day ago
The Shire Woodstock
North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"It was amazing my favorite place to go"
Jessica 1-night trip
Posted 1 day ago
North Star Lodge and Resort
Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Great place, we stopped for a few days while taking a break from hiking the AT. The grounds are amazing, breakfast was delicious, and staff was very accommodating. They even washing our stinky hiking clothes and picked up a pizza for us. Would highly recommend!"
Matthew 1-night trip
Posted 1 day ago
Mountain Meadows Lodge
Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Very clean nice place"
Michelle 2-night trip
Posted 2 days ago
Sleep Woodstock Motel
On The River Inn

On The River Inn

10/10 Excellent
"Everything was good I cannot complain"
Graziella 1-night trip
Posted 3 days ago
On The River Inn

More cheap stays in Pittsfield

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

401 US-7 Rutland VT
￥18,832
￥20,714 total
Aug 23 - Aug 24
includes taxes & fees
Days Inn by Wyndham Rutland/Killington Area
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
￥19,533
￥21,486 total
Aug 16 - Aug 17
includes taxes & fees
Comfort Inn Rutland - Killington
Sleep Woodstock Motel

Sleep Woodstock Motel

4324 West Woodstock Road Woodstock VT
￥14,345
￥21,916 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (602 reviews)
Sleep Woodstock Motel
Hampton Inn Rutland

Hampton Inn Rutland

47 Farrell Rd Rutland VT
￥20,792
￥22,870 total
Aug 30 - Aug 31
includes taxes & fees
Hampton Inn Rutland
The Mountain Inn at Killington

The Mountain Inn at Killington

47 Old Mill Rd Killington VT
￥19,939
￥23,032 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
The Mountain Inn at Killington
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
￥21,690
￥23,642 total
Sep 6 - Sep 7
includes taxes & fees
9.4/10 Exceptional! (524 reviews)
My Place Hotel-Randolph VT

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 17.9 mi (28.9 km) from the heart of Pittsfield, Woodstock Inn & Resort is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are The Mountain Inn at Killington and Killington Mountain Lodge, Tapestry Collection by Hilton. See all available top hotels, or vacation rentals in Pittsfield.
What's the top vacation rental in Pittsfield?
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak: This vacation home rental near Pittsfield is located on the waterfront and has a fireplace, a balcony, and cable TV to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of books. See all vacation rentals in Pittsfield.
If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.
Where can I learn more about changing or cancelling my trip to Pittsfield?
To find more details about changing or cancelling your trip to Pittsfield, go to https://www.expedia.com/service/.
What's the best pet-friendly place to stay in Pittsfield?
Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests. See more pet-friendly hotel accommodations in Pittsfield.
What are some accommodations with pools in Pittsfield?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. The Mountain Inn at Killington and Comfort Inn Rutland - Killington are a couple of other choices with an onsite pool. View all hotels with pools in Pittsfield.
What's the best accommodation near Rutland Southern Vermont Regional Airport (RUT)?
Comfort Inn Trolley Square is one of the top choices for your stay and is a popular hotel, featuring free breakfast and an indoor pool. It's located 4.9 mi (7.8 km) from Rutland Southern Vermont Regional Airport. Other choices near the airport include Holiday Inn Rutland-Killington Area and Quality Inn Rutland.
What's it like to stay in Pittsfield?
Visitors can enjoy all that Pittsfield has to offer including the bars and restaurants. This city also attracts tourists with its welcoming locals. In Pittsfield, there are 40 hotels and other accommodations to choose from. Find out more about Pittsfield.
What should I see while I'm in Pittsfield?
Favorite places to visit include Green Mountain National Forest, Roger Clark Memorial Central Library, and Pittsfield Town Hall. You'll also find Liberty Hill Farm and Green Mountain National Golf Course in the area. Check out what more to see and do in Expedia's Pittsfield guide.
What's the seasonal weather like in Pittsfield?
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.

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