A historic building with a prominent tower and an American flag.

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

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Our top choices for Pittsfield hotels

A cozy living area with a leather sofa, a wooden coffee table, and a patterned armchair. A brick wall and wooden shelves with various items are visible.

1. William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.4 out of 10, Exceptional, (383 reviews)
"Great place"
United States
Caroline
The price is ļæ„12,393
ļæ„13,631 total
includes taxes & fees
Nov 12 - Nov 13
William Watson Hotel
A hallway with wooden doors leading to a dining area with a table and chairs.

2. Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (153 reviews)
"Enjoyed our stay at Green Acres! When we return we will definitely stay there again"
United States
Kimberly
The price is ļæ„18,671
ļæ„20,535 total
includes taxes & fees
Dec 6 - Dec 7
Green Acres Hotel
A modern building with a white exterior, wooden deck, and a pergola with a railing.

3. Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.8 out of 10, Exceptional, (72 reviews)
"Best place Ive stayed period. 100 percent recommend"
United States
Isidro
The price is ļæ„17,512
ļæ„19,260 total
includes taxes & fees
Nov 10 - Nov 11
Monroe Street Suites
A bakery display with various baked goods and packaged snacks.

4. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (145 reviews)
"We stay everytime we are in town"
United States
Stephanie
The price is ļæ„10,911
ļæ„12,000 total
includes taxes & fees
Nov 30 - Dec 1
Rodeway Inn Pittsfield
A gazebo with a table and benches, surrounded by trees and a body of water.

5. River's Edge Motel

River's Edge Motel
2.0 star property
Louisiana
8.8 out of 10, Excellent, (395 reviews)
"Nice location."
United States
Jeff
The price is ļæ„13,154
ļæ„14,935 total
includes taxes & fees
Dec 8 - Dec 9
River's Edge Motel
A restaurant with a bar area, wooden flooring, checkered tablecloths, and a brick wall.

6. The Eagles Nest Inn

The Eagles Nest Inn
3.0 star property
Louisiana
9.6 out of 10, Exceptional, (28 reviews)
"Cutest place to stay in Louisiana Missouri"
United States
Kimberly
The price is ļæ„16,304
ļæ„18,511 total
includes taxes & fees
Nov 10 - Nov 11
The Eagles Nest 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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Stay near popular Pittsfield attractions

Old Orchard Country Club

8.8/10 (8 reviews)
This private 9-hole course challenges golfers with narrow fairways and water hazards across rolling terrain. Members enjoy practice facilities and a welcoming clubhouse restaurant after their round.
See properties

Learn more about Pittsfield

Nestled among rolling hills, Pittsfield invites history buffs to explore the John Greene Shastid House and Pike County Historic Museum. After delving into local heritage, visitors can unwind with a peaceful afternoon at King Park or tee off at nearby Old Orchard Country Club.

See all hotels in Pittsfield
A historic building with a prominent tower and an American flag.

Top Pittsfield Hotel Reviews

William Watson Hotel

William Watson Hotel

10/10 Excellent
"Great place"
Caroline 2-night trip
Posted 7 days ago
William Watson Hotel

More cheap stays in Pittsfield

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

1238 W Washington St Pittsfield IL
The price is ļæ„10,911 per night from Nov 30 to Dec 1
ļæ„10,911
ļæ„12,000 total
Nov 30 - Dec 1
includes taxes & fees
6.8/10 (145 reviews)

Frequently asked questions

Where is the best place for a stay in Pittsfield?
William Watson Hotel is one of the top choices for your stay based on our traveler data. This hotel offers free parking and a fitness center. Other good options for your stay include Rodeway Inn Pittsfield and Monroe Street Suites. 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. Some other top choices in Pittsfield are Family-Friendly Lakefront Cabin | Water Fun, Fire Rings & Open Lawns and Waterfront Cottage | Steps from Pine Lake & Resort Amenities | Ideal Family Stay. 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 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 Pittsfield 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 are some accommodations with pools in Pittsfield?
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Offers sun loungers, a pool, and complimentary wireless internet access. Pine Lakes Adventure Stay | Waterpark, Fishing & Lakefront Fun | Lake Views and Family Escape | 2 Units | Lakefront Cabin, Seasonal Pool & Water Activities are a couple of other choices with an onsite pool. View all hotels with pools in Pittsfield.
What's the top hotel in Pittsfield with an on-site water park or a water park nearby?
Pine Lakes Cottage Retreat | Nature Trails & Lakeside Fun | Ideal for Families is a popular cabin featuring in-room kitchens and water park access. Another top water park hotel you might want to consider is 2 Units | Family Adventure Escape | Lakefront Fun, Pool & Water Obstacles. Check out all hotels with or near waterparks 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 40 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 King Park and Old Orchard Country Club. 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 73Ā°F, while the coldest months are January and February with an average of 34Ā°F. Average annual precipitation for Pittsfield is 46 inches.

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