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Top 10 Pittsfield hotels and places to stay

Exterior
William Watson Hotel
3.0 star property
9.0 out of 10, Wonderful, (298)
"This is the most quaint and precious little boutique hotel. It is located right on the square. My room had a perfect view of the local city hall. Both the lobby and my room were decorated with original time-oriented pieces. I absolutely LOVED this place and will definitely stay here again!!"
The price is CA $131
CA $145 total
includes taxes & fees
May 22 - May 23
William Watson Hotel
Lobby sitting area
Green Acres Hotel
2.5 star property
8.6 out of 10, Excellent, (111)
"Room was excellent and very comfortable! Couldn’t ask for more! Fran"
The price is CA $163
CA $179 total
includes taxes & fees
May 15 - May 16
Green Acres Hotel
Lobby sitting area
Monroe Street Suites
2.5 star property
9.6 out of 10, Exceptional, (45)
"Very satisfying experience."
The price is CA $102
CA $112 total
includes taxes & fees
May 19 - May 20
Monroe Street Suites
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Exterior
Rodeway Inn
2.0 star property
6.8 out of 10, (96)
"The owners were great,very nice!!"
The price is CA $82
CA $90 total
includes taxes & fees
May 19 - May 20
Rodeway Inn
Fridge, microwave, oven, stovetop
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
10.0 out of 10, Exceptional, (43)
"Our family had a great stay in IL. The house was excellent and the llamas were an added entertainment . Would definitely come back to stay!!"
The price is CA $272
CA $301 total
includes taxes & fees
Jun 7 - Jun 8
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Fridge, microwave, oven, stovetop
Buckhorn Barndo &Nature Retreat-near SiloamSprings
Buckhorn Barndo &Nature Retreat-near SiloamSprings
Interior
Idyllic Mt Sterling Retreat w/ Private Lake!
2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
Interior
Idyllic Mt Sterling Retreat w/ Private Lake!
10.0 out of 10, Exceptional, (3)
"Comfortable and well-equipped home, with more than enough towels. Under-advertised as has 2 1/2 baths, and use of the boathouse. Loved swimming and jumping off the dock, fishing, and just trolling around the lake with the two boats with trolling motors, and the peddle boat. Very wide mowed path around the lake and other trails. Also had marshmallow forks for the s’mores around the campfire. Enjoyed the rocking bench at the end of the dock, especially in the early morning and for watching...
Idyllic Mt Sterling Retreat w/ Private Lake!
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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.

Frequently asked questions

Where is the best place for a stay in Pittsfield?

Monroe Street Suites is a favorite property for Expedia customers. This hotel offers free parking and free WiFi. Traveler reviews also recommend William Watson Hotel and Green Acres Hotel as top choices for your stay. See all available top hotels, or vacation rentals in Pittsfield.

What's the top vacation rental that Pittsfield has to offer?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Visitors like this Pittsfield vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. Our travelers also rate River Cottage Along the Illinois River. as a favorite home for rent in Pittsfield. See all vacation rentals in Pittsfield.

If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?

Yes, you'll find most room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within a 24-hour period 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?

For more information about picking new dates or cancelling your trip to Pittsfield, click here.

What's the best budget-friendly hotel in Pittsfield?

Based on reviews, William Watson Hotel is a popular 3-star property for our travelers looking for an economical choice, and features free on-the-go breakfast and free WiFi. View all budget hotels in Pittsfield.

What's the best accommodation for families in Pittsfield?

Rodeway Inn is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. Other good options for your kid-friendly vacation include Monroe Street Suites and Green Acres Hotel. Find more child-friendly accommodations in Pittsfield.

What is the favorite LGBTQ-friendly hotel in Pittsfield?

William Watson Hotel is a top LGBTQ-friendly hotel that features free parking and a fitness center. See all available hotels listed as LGBTQ-friendly in Pittsfield.

What's the best pet-friendly place to stay in Pittsfield?

Rodeway Inn is a top hotel for people traveling with their pets, and offers free WiFi for its human guests. See more pet-friendly hotel accommodations in Pittsfield.

Where is the best hotel to stay near Old Orchard Country Club?

Green Acres Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located 2.4 mi (3.9 km) from Old Orchard Country Club. Other good choices within 5 miles include William Watson Hotel and Monroe Street Suites.

What's the best boutique-style hotel in Pittsfield?

William Watson Hotel is a favorite 3-star hotel with our travelers looking for a stylish accommodation, featuring 14 guestrooms, free parking, and free WiFi. See all boutique hotels in Pittsfield.

What are some accommodations with pools in Pittsfield?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Provides sun loungers, a pool, and complimentary wireless internet access. View all hotels with pools in Pittsfield.

How is it to stay in Pittsfield?

Visitors can enjoy all that Pittsfield has to offer including the cafes, entertainment choices, and breweries. Tourists can also enjoy so much more including its theaters. In Pittsfield, there are 10 hotels and other accommodations to choose from. Find out more about Pittsfield.

What is there to see in Pittsfield?

Cultural venues include John Greene Shastid House and Pike County Historic Museum. A couple of additional sights to add to your agenda are Old Orchard Country Club and King Park. Check out what more to see and do in Expedia's Pittsfield guide.

What's the weather like in Pittsfield?

The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Pittsfield is 46 inches.