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Top 10 trending Pittsfield hotels

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, (910)
"Loved the gluten free options in the Breakfast nook"
The price is P5,391
P5,930 total
includes taxes & fees
Jul 31 - Aug 1
Mountain Sports Inn
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, (505)
"Cozy and comfortable stay!"
The price is P5,265
P6,737 total
includes taxes & fees
Aug 6 - Aug 7
Sleep Woodstock Motel
Middlebury Sweets Motel
Two single beds with wooden headboards and colorful pillows, a nightstand with a lamp, and a small table with a book and decorative item.

Middlebury Sweets Motel

2.5 star property
8.6 out of 10, Excellent, (363)
"Such a great place with great management "
The price is P7,255
P7,981 total
includes taxes & fees
Jul 31 - Aug 1
Middlebury Sweets Motel
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (27)
"Charming Inn with beautiful gallery and family owned"
The price is P7,976
P8,775 total
includes taxes & fees
Aug 6 - Aug 7
Lincoln Inn & Gallery
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, (38)
"Superb stay in all ways!"
The price is P14,280
P15,708 total
includes taxes & fees
Aug 7 - Aug 8
Stay At Jimmy's
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, (238)
"Very nice place to stay would return"
The price is P9,283
P10,118 total
includes taxes & fees
Aug 12 - Aug 13
My Place Hotel-Randolph VT
Mountain Valley Retreat
Stunning two-story house with a gabled roof and wrap-around porch, set amidst a beautifully manicured lawn and lush trees.

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (181)
"Great experience. Very accommodating! Room was great! Everything was clean and homemade breakfast was amazing. Thanks "
The price is P6,308
P7,128 total
includes taxes & fees
Jul 31 - Aug 1
Mountain Valley Retreat
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, (1000)
"Good value hotel in an excellent location."
North Star Lodge and Resort
Greenbrier Inn
A warm and inviting dining area with a vase of fresh foliage and a box of tea.

Greenbrier Inn

2.0 star property
9.6 out of 10, Exceptional, (608)
"nice place quiet "
Greenbrier Inn
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, (528)
"Relaxing "
The price is P25,749
P30,847 total
includes taxes & fees
Aug 17 - Aug 18
Woodstock Inn & Resort
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, (847)
"Great view, clean comfortable room."
The Mountain Inn at Killington
The Vesper
Relax in this serene bedroom with a large bed, two windows, and a cozy reading nook.

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (24)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is P10,753
P11,828 total
includes taxes & fees
Jul 31 - Aug 1
The Vesper
The Lilac Inn
Stately building with a central entrance and beautifully landscaped grounds.

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (195)
"I love staying at the Lilac Inn when visiting family in the area. "
The price is P13,133
P14,446 total
includes taxes & fees
Jul 31 - Aug 1
The Lilac Inn
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, (928)
"The staff were helpful and morning breakfast very good. "
The price is P10,638
P11,702 total
includes taxes & fees
Aug 10 - Aug 11
Hampton Inn Rutland
The Jackson
1 bedroom, down comforters, individually decorated

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (223)
"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. "
The Jackson
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, (494)
"Excellent stay!!"
The price is P8,648
P9,513 total
includes taxes & fees
Jul 31 - Aug 1
Brandon Inn
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, (792)
"Clean, comfortable rooms with a great view of the river. Easy to walk to the downtown Woodstock area and friendly staff. "
The Shire Woodstock
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, (1022)
"I believe I already submitted a review, but this was a great place to stay, convenient, clean, and friendly."
The price is P7,174
P7,892 total
includes taxes & fees
Aug 18 - Aug 19
Comfort Inn Rutland - Killington
Emrose Luxury Cabins
Blackout drapes, free WiFi, bed sheets

Emrose Luxury Cabins

2.0 star property
9.0 out of 10, Wonderful, (39)
"The customer service was excellent!"
The price is P9,263
P10,467 total
includes taxes & fees
Aug 14 - Aug 15
Emrose Luxury Cabins
The Trailside Inn
Welcome to Trailside Inn, situated amidst a serene natural setting with a lodge-style building and ample parking.

The Trailside Inn

3.0 star property
9.0 out of 10, Wonderful, (131)
"Such a great, comfortable place to stay with an awesome staff!"
The price is P9,136
P10,049 total
includes taxes & fees
Aug 7 - Aug 8
The Trailside 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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Learn more about Pittsfield

Explore Pittsfield: its bars and more!

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Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"Wonder stay. Clean and very comfortable "
Kimberly 1-night trip
Posted 3 days ago
My Place Hotel-Randolph VT

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.