Pittsfield Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 13 - Jul 14
Tomorrow
Jul 14 - Jul 15
Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Pittsfield hotels

Days Inn by Wyndham Rutland/Killington Area
Relax in a spacious room with a large bed, two bedside tables, and a beautiful landscape painting above.

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
6.4 out of 10, (1003)
"we like the pool and the room is ok. "
The price is P5,810
P6,391 total
includes taxes & fees
Jul 20 - Jul 21
Days Inn by Wyndham Rutland/Killington Area
Comfort Inn Rutland - Killington
Enjoy a refreshing swim in our indoor pool, surrounded by a decorative border and adjacent to a hot tub.

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very Good, (1005)
"I believe I already submitted a review, but this was a great place to stay, convenient, clean, and friendly."
The price is P7,066
P7,773 total
includes taxes & fees
Jul 20 - Jul 21
Comfort Inn Rutland - Killington
Best Western Inn & Suites Rutland-Killington
Enjoy meals or drinks at the dining table, with easy access to the outdoor patio area.

Best Western Inn & Suites Rutland-Killington

2.5 star property
8.8 out of 10, Excellent, (1002)
"Easy to find, room clean and would stay again if I needed a room in this area. "
The price is P9,609
P10,570 total
includes taxes & fees
Jul 20 - Jul 21
Best Western Inn & Suites Rutland-Killington
Sleep Woodstock Motel
Cozy living area with a fireplace, comfortable seating, and a staircase leading to an upper level.

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (499)
"This place was lovely, they were always checking in to make sure we were ok and they had plenty of amenities for us to use!"
The price is P5,287
P6,748 total
includes taxes & fees
Jul 15 - Jul 16
Sleep Woodstock Motel
Woodstock Inn & Resort
Stately room with a checkered floor, classic bench, and fireplace view.

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (523)
"Relaxing "
The price is P25,927
P31,005 total
includes taxes & fees
Aug 10 - Aug 11
Woodstock Inn & Resort
The Shire Woodstock
Surrounded by lush forests and a meandering river, this picturesque village offers a serene escape.

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (776)
"Great location!! Very accommodating and clean."
The Shire Woodstock
Cortina Inn
Convenient fueling station with seating and amenities.

Cortina Inn

3.0 star property
6.8 out of 10, (567)
"Staff were extremely helpful all during my stay."
The price is P5,592
P6,151 total
includes taxes & fees
Jul 14 - Jul 15
Cortina Inn
My Place Hotel-Randolph VT
Fully equipped kitchen with a refrigerator, sink, microwave, and coffee maker.

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (221)
"Very nice accommodations and convenient location."
The price is P9,342
P10,183 total
includes taxes & fees
Jul 20 - Jul 21
My Place Hotel-Randolph VT
Hampton Inn Rutland
Welcome to the Hampton Inn, featuring a modern exterior with a prominent sign and covered walkway to the lobby, set amidst a beautifully maintained landscape.

Hampton Inn Rutland

2.5 star property
9.0 out of 10, Wonderful, (924)
"Easy check in, close to everything, clean, large room, pet friendly, friendly staff…We’ve stayed here a few times, and it’s very nice! Room rates are reasonable too! "
The price is P11,047
P12,152 total
includes taxes & fees
Jul 27 - Jul 28
Hampton Inn Rutland
Brandon Inn
Stunning hotel entrance with a traditional marquee sign, set amidst snow-covered trees and a charming sidewalk.

Brandon Inn

3.0 star property
8.6 out of 10, Excellent, (482)
"An extremely charming hotel, wonderful choices for breakfast, and close to dining and a grocery store. "
The price is P8,518
P9,370 total
includes taxes & fees
Jul 27 - Jul 28
Brandon Inn
The Mountain Inn at Killington
Experience the warm ambiance of this distillery, featuring a prominent entrance, large windows, and outdoor seating areas.

The Mountain Inn at Killington

2.5 star property
9.2 out of 10, Wonderful, (832)
"Great place to stay with kids. Our boys loved the pool and the games room. "
The Mountain Inn at Killington
Courtyard Middlebury
Classic hotel with a central entrance and two wings, featuring a well-maintained facade and multiple windows.

Courtyard Middlebury

3.0 star property
8.8 out of 10, Excellent, (518)
"Good location for hiking and going to Middlebury College "
The price is P8,083
P8,891 total
includes taxes & fees
Jul 20 - Jul 21
Courtyard Middlebury
Mountain Meadows Lodge
Surrounded by vibrant fall colors and a majestic mountain range, this serene lakeside setting offers a tranquil escape.

Mountain Meadows Lodge

3.5 star property
9.4 out of 10, Exceptional, (132)
"Great views great hiking and a beautiful area. Was very clean and well maintained."
The price is P8,416
P10,670 total
includes taxes & fees
Jul 14 - Jul 15
Mountain Meadows Lodge
Stay At Jimmy's
Relax in a serene space with a large mirror, plush seating area, and a touch of greenery.

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (35)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
The price is P14,065
P15,472 total
includes taxes & fees
Jul 14 - Jul 15
Stay At Jimmy's
North Star Lodge and Resort
Two single beds with made bedspreads and pillows, a large window with blinds, and wall-mounted paintings create a clean and inviting space.

North Star Lodge and Resort

2.0 star property
8.6 out of 10, Excellent, (1001)
"Good value hotel in an excellent location."
North Star Lodge and Resort
On The River Inn
Enjoy cooking in this well-equipped kitchen with a dishwasher, microwave, stove, and refrigerator, plus a convenient island with sink and countertop workspace.

On The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1002)
"Wonderful place to stay. "
The price is P10,687
P13,827 total
includes taxes & fees
Jul 14 - Jul 15
On The River Inn
Mountain Sports Inn
Enjoy a relaxing stay with a hot tub and sauna on the upper balcony.

Mountain Sports Inn

2.0 star property
8.8 out of 10, Excellent, (902)
"The location was so quiet and nice."
The price is P5,310
P5,841 total
includes taxes & fees
Jul 14 - Jul 15
Mountain Sports Inn
The Mountain Top Inn & Resort
Relax in a spacious living area with a leather sofa, wooden coffee table, and expansive windows offering a view of the surrounding landscape.

The Mountain Top Inn & Resort

3.5 star property
9.2 out of 10, Wonderful, (85)
"Great views and food. "
The price is P18,358
P23,012 total
includes taxes & fees
Jul 14 - Jul 15
The Mountain Top Inn & Resort
Killington Mountain Lodge, Tapestry Collection by Hilton
Experience the unique architecture and tranquil courtyard with a swimming pool and waterfall, surrounded by seating areas and balconies.

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1003)
"Pleasant stay "
The price is P8,106
P8,916 total
includes taxes & fees
Jul 20 - Jul 21
Killington Mountain Lodge, Tapestry Collection by Hilton
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (18)
"Lovely little inn with a picturesque setting. "
The price is P6,778
P7,456 total
includes taxes & fees
Jul 15 - Jul 16
Lincoln Inn & Gallery
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Pittsfield

Explore Pittsfield: its bars and more!

See all hotels in Pittsfield

Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Woodstock Inn & Resort and North Star Lodge and Resort. See all available top hotels, or 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 budget-friendly hotel in Pittsfield?

Based on reviews, Clear River Inn is a popular inn for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Pittsfield.

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?

Comfort Inn Rutland - Killington: Features continental, an indoor pool, and free self parking. Woodstock Inn & Resort and North Star Lodge and Resort 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 44 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 Green Mountain National Golf Course and Gifford Woods State Park 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.