Hotels in Pittsfield from P5,354 for 2025 - Fully Refundable Options

Top 10 trending Pittsfield hotels

Enjoy a relaxing stay with a hot tub and sauna on the upper balcony.

"Loved the gluten free options in the Breakfast nook"

P6,014 total

includes taxes & fees

Aug 3 - Aug 4

Cozy living area with a fireplace, comfortable seating, and a staircase leading to an upper level.

"Cozy and comfortable stay!"

P6,852 total

includes taxes & fees

Aug 5 - Aug 6

Two single beds with wooden headboards and colorful pillows, a nightstand with a lamp, and a small table with a book and decorative item.

"Such a great place with great management "

P9,853 total

includes taxes & fees

Aug 3 - Aug 4

"Charming Inn with beautiful gallery and family owned"

P12,092 total

includes taxes & fees

Aug 17 - Aug 18

Relax in a serene space with a large mirror, plush seating area, and a touch of greenery.

"Superb stay in all ways!"

P15,931 total

includes taxes & fees

Aug 7 - Aug 8

Fully equipped kitchen with a refrigerator, sink, microwave, and coffee maker.

"Very nice place to stay would return"

P10,486 total

includes taxes & fees

Aug 10 - Aug 11

Stunning two-story house with a gabled roof and wrap-around porch, set amidst a beautifully manicured lawn and lush trees.

"Great experience. Very accommodating! Room was great! Everything was clean and homemade breakfast was amazing. Thanks "

P7,230 total

includes taxes & fees

Aug 4 - Aug 5

Two single beds with made bedspreads and pillows, a large window with blinds, and wall-mounted paintings create a clean and inviting space.

"Good value hotel in an excellent location."

A warm and inviting dining area with a vase of fresh foliage and a box of tea.

"nice place quiet "

Stately room with a checkered floor, classic bench, and fireplace view.

"Relaxing "

P28,727 total

includes taxes & fees

Sep 1 - Sep 2

Experience the warm ambiance of this distillery, featuring a prominent entrance, large windows, and outdoor seating areas.

"Great view, clean comfortable room."

Relax in this serene bedroom with a large bed, two windows, and a cozy reading nook.

"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"

P12,596 total

includes taxes & fees

Aug 5 - Aug 6

Stately building with a central entrance and beautifully landscaped grounds.

"I love staying at the Lilac Inn when visiting family in the area. "

P14,652 total

includes taxes & fees

Aug 3 - Aug 4

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.

"The staff were helpful and morning breakfast very good. "

P9,735 total

includes taxes & fees

Sep 1 - Sep 2

Stroll through the serene garden, surrounded by lush greenery and a tranquil atmosphere.

"A quaint boutique historic hotel with a cool little bar and fine dining. The view from our room overlooking the garden and lush lawn added to the tranquil atmosphere that we were hoping for. The owners were pleasant and friendly. "

Stunning hotel entrance with a traditional marquee sign, set amidst snow-covered trees and a charming sidewalk.

"Excellent stay!!"

P9,648 total

includes taxes & fees

Aug 3 - Aug 4

Surrounded by lush forests and a meandering river, this picturesque village offers a serene escape.

"Clean, comfortable rooms with a great view of the river. Easy to walk to the downtown Woodstock area and friendly staff. "

Enjoy a refreshing swim in our indoor pool, surrounded by a decorative border and adjacent to a hot tub.

"Great location."

P8,004 total

includes taxes & fees

Aug 18 - Aug 19

"The customer service was excellent!"

P10,648 total

includes taxes & fees

Aug 4 - Aug 5

Welcome to Trailside Inn, situated amidst a serene natural setting with a lodge-style building and ample parking.

"Such a great, comfortable place to stay with an awesome staff!"

P10,192 total

includes taxes & fees

Aug 4 - Aug 5

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Top Pittsfield Hotel Reviews

Woodstock Inn & Resort

10/10 Excellent

"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

The Jackson

10/10 Excellent

"The inn was marvelous. The inn keeper and her husband the maintenance man were charming and responsive to our needs and kept the place immaculate. The restaurant was dissapointing. Service was terrible, eggs were over cooked. Toast was slathered in butter (I think it was butter). No salt, pepper or any other condiments were on the table and the waitress was no where to be found so we ate the meal as it was getting cold. We did not go back the next day"

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent

"THE STAFF WAS AMAZING, COULDN'T BE MORE HELPFUL, THE BREAKFAST WAS MORE THAN SUFFICIENT & PLENTYFUL. IT WAS NOT EVEN TAKING DOWN UNTIL AFTER 9:30 AM!!! THE CLEANING STAFF NEED TO PAY MORE ATTENTION TO CLEANING BEHIND & UNDER THE BED. PUT THE REST OF THE ROOM SEEMED CLEAN. THANK YOU FOR A GREAT VISIT THE ROOM C"

More cheap stays in Pittsfield

Comfort Inn Rutland - Killington

19 Allen St, Rutland, VT

P7,276

P8,004 total

Aug 18 - Aug 19

includes taxes & fees

8/10 Very Good! (1,000 reviews)

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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 Killington Mountain Lodge, Tapestry Collection by Hilton. 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.

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Top 10 trending Pittsfield hotels

Mountain Sports Inn

Mountain Sports Inn

Sleep Woodstock Motel

Sleep Woodstock Motel

Middlebury Sweets Motel

Middlebury Sweets Motel

Lincoln Inn & Gallery

Lincoln Inn & Gallery

Stay At Jimmy's

Stay At Jimmy's

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

Mountain Valley Retreat

Mountain Valley Retreat

North Star Lodge and Resort

North Star Lodge and Resort

Greenbrier Inn