Best-rated hotels in Pittsfield for your unforgettable stay

Detailed descriptions, travelers’ reviews, and handpicked hotel collections will help you book your perfect accommodation.

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Choose from exclusive hotel collection

We offer thousands of Pittsfield hotels and accommodations from world's renowned hotel chains to unique gems of the region you won’t find anywhere else.

Enjoy seamless booking experience

Once you choose your best place to stay, take a minute to complete a quick reservation form and get an instant confirmation letter to your email address.

Benefit from flexible travel options

We provide the most flexible cancellation options, so you get your deposit back in case of a change of plans or other unforeseen circumstances.

Find a hotel

Hotels by class
4 stars 2
3 stars 2
2 stars 2
Unrated 1
Accommodation type
Hotels 5
Campsite 1
Inn 1
Thematic Hotels
Historical hotels 3
Golf hotels 3
Central hotels 3
Business hotels 3
Pet-friendly hotels 2
Luxury accommodations 2
Luxury hotels 2
Family Friendly hotels 1
Cheap and budget hotels 1
Hotels with indoor pool 1
All Pittsfield hotels

Hotels by location

Nearby
City Center Pittsfield 4
Pike County Historical Society 4
Nature House Showcase 4
Landmarks
Museums
Popular attractions
Illinois >
Pittsfield

Welcome to Pittsfield

Discover the charm of Pittsfield, a vibrant city nestled in the heart of Massachusetts. Immerse yourself in its rich history at the Berkshire Museum or take a leisurely stroll through the picturesque downtown. Indulge in the diverse culinary scene or explore the beautiful hiking trails in the surrounding mountains. Embrace the captivating culture and warm hospitality of Pittsfield - an experience waiting to be uncovered. Visit Pittsfield and ignite your sense of adventure!

What our users say about Pittsfield hotels

Warwick Allerton Chicago
9.8

Exceptional

us Ethel 07 September 2022
Fancy brand-new hotel in the middle of Chicago.
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Central Loop Hotel
9.8

Exceptional

us Ann 07 October 2022
Spotless, recently refurbished hotel, it has perfect staff and location. It is set in a central area, walking distance to a church and an art gallery.
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Eurostars Magnificent Mile
9.8

Exceptional

us Susan 14 July 2022
I liked this trendy boutique hotel and stayed for 2 nights here. I've booked king room with fantastic views and everything was perfect.
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Embassy Suites By Hilton Chicago Downtown Magnificent Mile
9.8

Exceptional

us William 14 November 2022
It was the best of Chicago hotels I visited before now. For a 4 star hotel everything was amazing, I appreciated to be here. The staff were attentive and accommodating. The location was stunning, a 10-15 minute walking distance from Chicago Water Tower.
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River Hotel
9.8

Exceptional

us Craig 13 December 2022
Enjoyed staying here. the staff were great and the location was convenient. Loads of dining options and bars nearby to grab a bite to eat or have a drink 🍹.
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Raffaello Chicago
9.8

Exceptional

us Liz 14 August 2022
The hotel was fairly clean. the location was stunning near Michigan Avenue with easy access to most shops. - I liked the updated and cozy room with a nice view. - the staff were accommodating and exceptional in every interaction we had.
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Hotel Saint Clair - Magnificent Mile
9.8

Exceptional

us Joshua 23 December 2022
The hotel is clean and budget-friendly. Located conveniently close to restaurants. The rooms are newly decorated and functional. Friendly and helpful staff at the reception desk.
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Freehand Chicago
9.8

Exceptional

us Curtis 15 February 2023
Clean rooms with air conditioning and a private bathroom, plus free WiFi 🌟.
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Hotel Felix
9.8

Exceptional

us Harry 23 August 2021
We loved this interesting place and its unbeatable location. The room we had was contemporary where toilet did n't flush. It had superb rooftop restaurant.
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Hyatt Regency Chicago
9.8

Exceptional

us Ralph 02 November 2022
I had a great time during my 2-night stay here, the location was perfect, just a short walk to Riverwalk, and the breakfast options were fantastic.
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Save time on your trip arrangements by booking one of our hand-picked hotels

Best 4-star hotels
Exclusive 3-star hotels
Quality 2-star hotels
Experience the best value for your money by checking out our selection of 4-star Pittsfield hotels.
Overlook Farm Inns

901 South Hwy 79, Pittsfield, United States

William Watson Hotel (Adults Only)

105 East Washington Street, Pittsfield, United States

79 US$

min. price/night

Enjoy truly authentic experiences without compromising comfort and convenience.
Green Acres Hotel

625 W Washington, Pittsfield, United States

Excellent
39 reviews

89 US$

min. price/night

Amee Farm Lodge

4275 Vt-100, Pittsfield, United States

Discover the hidden gems of Pittsfield by booking one of its budget-friendly hotels.
Rodeway Inn Pittsfield

1238 W. Washington St., Pittsfield, United States

Acceptable
16 reviews

71 US$

min. price/night

Monroe Street Suites

221 S Monroe St, Pittsfield, United States

75 US$

min. price/night

Travelers’ choice

Check out the most booked accommodations to find reliable places that our users have tried and tested.
Jellystone Park At Pine Lakes

1405 Lakeview Heights, Pittsfield, United States

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