Hotels in Pittsfield
Search over 34 hotels from $64
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Top Rated Pittsfield Hotels

William Watson Hotel

Green Acres Hotel

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Rodeway Inn

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Monroe Street Suites

Upgraded farmhouse between Springfield Illinois and St.Lous Missouri

Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake.

West Central Lodging

River's Edge Motel

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

The Eagles Nest Inn
Top reasons to visit Pittsfield
- Outdoor Adventures: Explore the breathtaking Pike County countryside, go hunting or birdwatching, and enjoy the local wildlife. It's the perfect destination for an outdoor vacation!
- Historical Landmarks: Immerse yourself in history by visiting the Pike County Courthouse and the Old Orchard Museum. Step back in time and learn about the town's rich heritage.
- Cultural Performances: Experience the vibrant local culture with live performances at the Pike County Opera House or catch a show at the historic Pittsfield Theater. Entertainment awaits!
- Cozy Cafes: Savor a cup of joe at the town's cozy cafes. Enjoy the relaxed atmosphere and indulge in delicious coffee concoctions.
- Local Brews: Beer enthusiasts, rejoice! Sample the finest local brews at nearby breweries. Cheers to a delicious and refreshing experience!
Popular hotels in Pittsfield
Pittsfield, Illinois, a charming destination for outdoor enthusiasts, offers a variety of hotel accommodations to suit every traveler's needs. From cozy bed and breakfasts to modern hotels, there is something for everyone. Whether you're looking for a budget-friendly option or a luxurious stay, Pittsfield has it all. Explore the beautiful surroundings and enjoy the comfort of the best hotels in Pittsfield. Check out the hotel map to find the perfect location for your outdoor adventure.
- Super 8 by Wyndham Bowling Green - Super 8 by Wyndham Bowling Green is a 2.0-star rated hotel located 27.5 miles away from Pittsfield. This hotel is a good option for your outdoor vacation because it offers free breakfast, pet-friendly accommodations, and free parking. Its close proximity to the outdoors makes it convenient for outdoor activities. Additionally, the hotel provides a microwave for your convenience.
- River's Edge Motel - River's Edge Motel is a 2.0-star rated motel located 16.8 miles away from Pittsfield. This motel is a great choice for your outdoor vacation as it offers pet-friendly accommodations, a river view, and free parking. The motel's proximity to the river provides opportunities for relaxing and enjoying the natural surroundings. You can also take part in excursions and enjoy a riverview from the balcony.
- William Watson Hotel - William Watson Hotel is a 3.0-star rated hotel with a boutique, historical charm. It is a good option for your outdoor vacation as it offers free breakfast, pet-friendly accommodations, and laundry facilities. The hotel's close proximity to urban areas and shopping makes it convenient for exploring the city after your outdoor activities. Enjoy a drink at the hotel's bar and take advantage of business amenities if needed.
Top things to see and do in Pittsfield
Pittsfield, Illinois is a charming town with a variety of attractions that cater to all interests. For outdoor enthusiasts, Lake Pittsfield is a must-visit, offering opportunities for fishing, boating, and picnicking. History buffs will appreciate exploring top landmarks like the Pike County Courthouse and the Old Orchard Museum. For a taste of local culture, visitors can enjoy live performances at the Pike County Opera House or catch a show at the historic Pittsfield Theater. Coffee lovers can savor a cup of joe at the cozy cafes in town, while beer enthusiasts can sample local brews at the nearby breweries. Wildlife lovers will also enjoy birdwatching in the area. Whether you're in search of family-friendly activities or entertainment options, Pittsfield has something for everyone.
- Old Orchard Country Club: Nestled in the picturesque countryside, Old Orchard Country Club offers a serene escape for golf enthusiasts. Immerse yourself in the lush green fairways and enjoy the thrill of a challenging game. With its close proximity to hunting grounds and wildlife, this club offers a unique opportunity to combine outdoor adventure with sports. After a game, unwind at the club's opera and theater events, or simply savor a cup of coffee or beer while birdwatching. Old Orchard Country Club is the perfect blend of relaxation and excitement.
- King Park: Located in the heart of the city, King Park is a vibrant urban oasis that caters to families and outdoor enthusiasts alike. Take a leisurely stroll through the park's well-manicured grounds, surrounded by architectural marvels. With its proximity to hunting and wildlife, King Park offers a unique blend of nature and city experiences. Enjoy family-friendly entertainment, opera, and theater performances, or simply unwind at a nearby bar with a refreshing beer. King Park is the perfect destination to immerse yourself in the charm of the city while enjoying the great outdoors.
- John Greene Shastid House: Step back in time and discover the rich history of the John Greene Shastid House. This magnificent historic house showcases stunning architecture and offers a glimpse into the past. Explore the house's elegant interiors and admire its intricate details. With its proximity to hunting and wildlife, this attraction allows you to experience the natural beauty of the surroundings while immersing yourself in culture. Whether you're interested in opera, theater, or birdwatching, the John Greene Shastid House provides a unique opportunity to delve into history and enjoy a refreshing beer in a historical setting.
Best places to visit in Pittsfield
Pittsfield, Illinois offers a plethora of outdoor adventures. Explore the breathtaking Pike County countryside, go hunting or birdwatching, and enjoy the local wildlife. Afterward, relax at one of the cozy cafes or breweries in the area. It's the perfect destination for an outdoor vacation!
- Detroit: Detroit is a city that has reinvented itself, offering a unique experience for outdoor enthusiasts. With its stunning riverfront and numerous parks, Detroit is an urban oasis for nature lovers. Explore Belle Isle Park, a 982-acre island park with beautiful views of the Detroit skyline. Take a walk along the Detroit Riverwalk, a scenic pathway that stretches for miles and offers breathtaking views of the river. For a taste of local flavor, visit Eastern Market, one of the largest and oldest public markets in the United States. Here, you can browse through a variety of fresh produce, artisanal goods, and local delicacies. Detroit's rich history, vibrant arts scene, and friendly atmosphere make it a must-visit destination for outdoor holiday.
- Time: Time is a city that is worth visiting for outdoor holiday. Nestled in the heart of the Berkshire Mountains, Time offers a picturesque and peaceful setting for outdoor activities. Explore the beautiful trails of Pittsfield State Forest, where you can hike, bike, or simply enjoy a picnic surrounded by nature. For water enthusiasts, Onota Lake is the perfect spot for boating, fishing, or swimming. Time also boasts a vibrant arts and culture scene, with numerous galleries, theaters, and music venues. Don't miss the opportunity to visit Tanglewood, the summer home of the Boston Symphony Orchestra, for a memorable outdoor concert experience. With its natural beauty and cultural attractions, Time is a hidden gem for outdoor holiday.
Seasonal travel trends of Pittsfield
The popularity of Pittsfield shows no change throughout the year. The most popular time to visit is between June and August, with a seasonal peak in July. The off-peak tourist season is from December and February, with January typically being the quietest month.
Check out the month-by-month weather chart for Pittsfield to help you plan your next trip. With a monthly average of 76.1 degrees Fahrenheit, you can expect the hottest temperatures in July. The coldest month, on average, is January. The most rainfall typically happens in May. Regardless of when you visit Pittsfield, every season has a reason to stay.
![]() | ![]() | ![]() | ![]() |
January | 28.0°F (-2.2°C) | Light Rain | Mostly Cloudy |
February | 31.1°F (-0.5°C) | Light Rain | Mostly Sunny |
March | 43.5°F (6.4°C) | Light Rain | Mostly Sunny |
April | 53.4°F (11.9°C) | Light Rain | Mostly Sunny |
May | 63.9°F (17.7°C) | Light Rain | Mostly Sunny |
June | 73.4°F (23.0°C) | Light Rain | Mostly Sunny |
July | 76.1°F (24.5°C) | Light Rain | Mostly Sunny |
August | 74.7°F (23.7°C) | Light Rain | Mostly Sunny |
September | 68.7°F (20.4°C) | Light Rain | Mostly Sunny |
October | 56.1°F (13.4°C) | Light Rain | Mostly Sunny |
November | 43.7°F (6.5°C) | Light Rain | Mostly Sunny |
December | 34.7°F (1.5°C) | Light Rain | Mostly Sunny |
What's the best place for a stay in Pittsfield?
What are the best pet-friendly hotels in Pittsfield?
Rodeway Inn is a pet-friendly hotel with free breakfast, free WiFi, and free parking.
What are some favorite hotels in central Pittsfield?
These are some of the most popular hotels in central Pittsfield:
- William Watson Hotel is a hotel offering free parking, a fitness center, and a snack bar/deli.
- Green Acres Hotel is a hotel offering free breakfast, free WiFi, and free parking.
- Monroe Street Suites is a hotel offering free WiFi, free parking, and flat-screen TVs.
Close to central Pittsfield, you'll find interesting places to visit like Old Orchard Country Club.
What are the best hotels to stay near King Park?
King Park is popular for a reason. Come and see just what makes this recreation and green space such a hit. Only 2 miles from the center of Pittsfield, it is close to a number of hotels. Spend your nights at William Watson Hotel (0.5 miles) and you'll be there in no time. Monroe Street Suites (0.6 miles away) and Green Acres Hotel (1 mile away) are two more great options in the vicinity.
Pittsfield hotels essential information
Accommodation | 34 hotels |
---|---|
Lowest Price | $64 |
Highest Price | $351 |
Popular hotels | William Watson Hotel, Green Acres Hotel, PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!, Rodeway Inn, Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland , Monroe Street Suites, Upgraded farmhouse between Springfield Illinois and St.Lous Missouri , Lovers’ Lakeside Love Nest Cozy Retreat on Pittsfields Serene Lake., West Central Lodging, River's Edge Motel, Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL , The Eagles Nest Inn |
Booking tips for Pittsfield
Booking tips for Pittsfield
Find your perfect hotel with Orbitz
We are committed to promoting inclusivity in travel, ensuring that your next trip is accessible to all. When searching for ideal accommodations, utilize our filters to discover eco-certified hotels or those that prioritize welcoming LGBTQ+ guests. Furthermore, our customized filters allow you to narrow down options based on proximity to top attractions, book now, pay later options, and more.
Travel as you are
At Orbitz, we embrace diversity and inclusion in travel. From our early LGBTQIA TV ads to supporting progressive charities, we have always been there. Our commitment remains strong, bringing people from all walks of life together to celebrate who they are and their destinations. Our goal is to create a welcoming world where everyone can travel with confidence and joy. We offer tools to help LGBTQIA+ travelers plan and book with assurance, including an LGBTQ-welcoming hotel filter that ensures you stay where you are celebrated, not just tolerated.
Saving tips for your trip
Save money by visiting Pittsfield during the less popular season from December to February. Take advantage of discounted prices by bundling your flights, hotel, and car bookings together. While in Pittsfield, you can enjoy inexpensive local activities such as birdwatching, visiting cafes, and exploring the wildlife. These options offer affordable entertainment and a chance to experience the natural beauty of the area without breaking the bank.
Recent Reviews

William Watson Hotel
Areas Of Pittsfield
Hotels Near
Hotel Themes
Book on Expedia
More to Explore
Top Trending
- Cheap Hotels in Peoria
- Hotels with Hot Tubs in Rockford
- Hotels with Hot Tubs in Elgin
- Hotels with Hot Tubs in Champaign
- Luxury Hotels in Springfield
- Cheap Hotels in Springfield
- Hotels in Champaign
- Hotels with Hot Tubs in Joliet
- Waterpark Hotels & Resorts in Galena
- Hotels with Hot Tubs in Decatur
- Hotels in Springfield
- Hotels with Hot Tubs in Collinsville
- Cheap Hotels in Champaign
- Hotels in Galena
- Hotels with Hot Tubs in Peoria
- Cheap Hotels in Galena
- Cheap Hotels in Joliet
- Romantic Getaways & Hotels in Galena
- Hotels with Hot Tubs in Ottawa
- Waterpark Hotels & Resorts in Springfield
- Hotels in Bloomington
- Hotels with Hot Tubs in Aurora
- Hotels with Hot Tubs in Marion
- Hotels with Hot Tubs in Springfield
- Hotels with Hot Tubs in Bloomington
- Hotels in Rockford