Pittsfield vacation rentals

We found 8 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Pittsfield that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a pool. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Pittsfield

Why visit Pittsfield

  • Outdoor Adventures: Enjoy stunning scenery with activities like hiking and picnicking in urban parks and nature preserves.
  • Family-Friendly Attractions: Discover a variety of attractions suitable for families, offering memorable experiences for all ages.
  • Scenic Waterfronts: Relax by picturesque rivers, perfect for leisurely strolls and outdoor fun.
  • Charming Accommodations: Choose from cozy cabins, spacious homes, or stylish apartments for the perfect stay.
  • Cultural Experiences: Immerse yourself in the local culture and sports, enriching your vacation in Pittsfield.

Popular types of accommodation in Pittsfield

Pittsfield offers a variety of vacation rentals to suit every traveler’s needs. From charming houses and cozy cabins to stylish apartments, you’ll find the perfect place to unwind. Whether you’re looking for a spacious house rental, a quaint cottage, or even a luxurious mansion, Pittsfield has options for everyone. Explore chic homes and discover the ideal base for your American getaway.

  • Houses: The most sought-after option for travelers in Pittsfield, these homes offer spacious and comfortable accommodations perfect for families, couples, or groups of friends.
  • Cabins: A favorite for those seeking a cozy escape, cabins provide a charming and rustic atmosphere, ideal for nature enthusiasts looking to unwind.
  • Apartments: These versatile living spaces are perfect for visitors seeking convenience and flexibility during their stay in Pittsfield.**

Top attractions near Pittsfield

Pittsfield, Illinois, is perfect for a family-friendly outdoor vacation, offering stunning scenery and a variety of attractions. Visitors can explore picturesque rivers, urban parks, and nature preserves that cater to those seeking cultural experiences and outdoor fun. Whether you're traveling solo, with friends, or family, Pittsfield has something for everyone to enjoy while immersing themselves in its natural beauty.

  • Mississippi River: Experience the majestic Mississippi River, located 19 miles from Pittsfield. Enjoy breathtaking scenery and immerse yourself in outdoor activities like fishing and boating, perfect for nature lovers.
  • Clarksville State Game Refuge: This 17-mile-away reserve offers a family-friendly atmosphere with friendly locals and opportunities for excursions. Relax in the natural beauty of the area, ideal for a peaceful day out.
  • Clarksville Riverfront Park: Just 17 miles from Pittsfield, this urban park is perfect for families. Enjoy outdoor activities while soaking in the vibrant city vibes along the riverfront.

Things to do recommended for couples

For a romantic getaway in Pittsfield, visit The Eagle's Nest Winery, located 17 miles away. Enjoy the charming ambiance and entertainment vibes while savoring exquisite wines together. It’s the perfect spot for couples looking to create memorable moments amidst beautiful surroundings.

Things to do recommended for families

Families visiting Pittsfield can explore the scenic hiking trails at the nearby Jim Edgar Panther Creek State Fish and Wildlife Area and enjoy a day of fun at the local parks, perfect for picnics and outdoor games. Don't miss the charming downtown with unique shops and eateries.

Things to do recommended for groups

Enjoy a day of golfing at Old Orchard Country Club, where your group can embrace the outdoor vibes and enjoy friendly competition on the greens. It's a perfect spot for relaxation and camaraderie in the picturesque setting of Pittsfield.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Pittsfield

If you're traveling with a group, with family, bringing along pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Pittsfield with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Pittsfield with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pittsfield: For many families, a vacation wouldn't be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and pet beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Pittsfield: If you're seeking vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Additionally, think about including features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Pittsfield

Pittsfield, Illinois, offers a delightful blend of outdoor adventures and family-friendly activities. Surrounded by scenic landscapes, visitors can explore nearby parks and waterfronts, perfect for leisurely strolls or picnics. The city is rich in culture and sports, making it an ideal destination for families seeking memorable experiences. Whether you're looking for cozy holiday houses or vibrant local attractions, Pittsfield is a fantastic base for your vacation exploration.

  • Griggsville: Located a mere 8 miles from Pittsfield, Griggsville is a charming city that invites visitors to immerse themselves in its stunning outdoor scenery. Known for its family-friendly atmosphere, the city offers a range of recreational activities, including a local golf course and a recreation center. Nature enthusiasts will appreciate the nearby national state park and picturesque lake, perfect for picnicking, hiking, or simply enjoying the great outdoors. Griggsville also hosts various events at its conference venue, making it a vibrant spot for both relaxation and recreation.
  • Nebo: Just 11 miles from Pittsfield, Nebo is an outdoor adventurer's paradise. With its breathtaking scenery and adventurous spirit, this city is ideal for those looking to explore the natural beauty of the region. Popular attractions include a recreational area and an entertainment arena, perfect for family fun and entertainment. Nearby, you'll find a national state park, a winding river, and historic sites that offer a glimpse into the area’s rich heritage. Nebo's welcoming charm makes it a perfect stop for both relaxation and adventure.
  • New Salem: Situated a short 7 miles from Pittsfield, New Salem offers a unique blend of cultural and business experiences. This city is rich in history and wellness opportunities, making it a great destination for those seeking a cultural immersion. Visitors can enjoy the local recreation center and explore historically significant landmarks, including a historic house and event conference venue. New Salem’s atmosphere is perfect for those looking to unwind while soaking in the area's deep-rooted heritage and communal spirit.

Best time to go to Pittsfield

If you're planning a trip to Pittsfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.0°F (-2.2°C)Light RainMostly CloudySlightly LowLow
February31.1°F (-0.5°C)Light RainMostly SunnySlightly LowLow
March43.5°F (6.4°C)Light RainMostly SunnyAverageAverage
April53.4°F (11.9°C)Light RainMostly SunnyAverageAverage
May63.9°F (17.7°C)Light RainMostly SunnyAverageAverage
June73.4°F (23.0°C)Light RainMostly SunnySlightly HighHigh
July76.1°F (24.5°C)Light RainMostly SunnySlightly HighHigh
August74.7°F (23.7°C)Light RainMostly SunnyAverageHigh
September68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
October56.1°F (13.4°C)Light RainMostly SunnyAverageAverage
November43.7°F (6.5°C)Light RainMostly SunnyAverageLow
December34.7°F (1.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to cut costs on your next trip? Consider being flexible with your travel dates, as prices can differ significantly. Also, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the total booking amount. Being the organizer truly has its benefits. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on eligible stays. Sign up today to start reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy-to-use platform where you can plan new trips, continue from where you last left off, or manage your travel arrangements. You’ll see your saved or booked properties neatly organized into categories: Potential, Upcoming, and Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The lively area of Pittsfield awaits your stay

Come and experience Pittsfield and its opera, entertainment and theater scene. Renowned for its wildlife, cafes and bird watching, this city welcomes all visitors. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Pittsfield

Do you want to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Pittsfield a fun spot to vacation. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Old Orchard Country Club (1.9 mi / 3.1 km)
  • The Eagle's Nest Winery (16.9 mi / 27.2 km)

Exploring the natural features in Pittsfield

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Pittsfield is a great place to get outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Clarksville Riverfront Park (17.1 mi / 27.6 km)
  • Mississippi River (19 mi / 30.6 km)
  • Clarksville State Game Refuge (16.9 mi / 27.1 km)
  • King Park (0.4 mi / 0.7 km)

Transportation options to and around Pittsfield

The nearest airport is in Quincy, IL (UIN-Quincy Regional-Baldwin Field), located 30.6 mi (49.3 km) from the city center.

Frequently asked questions

What is the best area to stay in Pittsfield when booking a vacation rental?
When considering a vacation rental in Pittsfield, Illinois, the downtown area is an excellent choice. This vibrant neighborhood offers a charming small-town atmosphere with a variety of shops, restaurants, and local attractions. Staying here puts you within walking distance of the historic Pittsfield Town Square, where you can enjoy community events and festivals throughout the year. Additionally, the nearby Pike County Courthouse showcases beautiful architecture and adds to the area's historical charm.

Another appealing option is the residential areas surrounding the picturesque Lake Pittsfield. This area is great for those who appreciate outdoor activities, as it provides opportunities for fishing, boating, and enjoying nature trails. The serene environment around the lake adds a peaceful backdrop to your stay, making it a great retreat after a day of exploring. The proximity to the lake also means you can easily visit the local parks, where you can relax or have a picnic.

In general, both of these areas offer a range of vacation rental properties, suiting various preferences and budgets.
How much does it cost to rent a vacation home in Pittsfield?
Prices for vacation rentals in Pittsfield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pittsfield to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pittsfield vacation house rentals?
You can find great discounts on house rentals in Pittsfield on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Pittsfield?
In Pittsfield, vacation houses are the most popular type of rental, with several available throughout the area. These homes typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups seeking a comfortable stay. Additionally, cabins are also a favored option, providing a more rustic experience with amenities such as fireplaces and outdoor decks for enjoying the natural surroundings. Apartments are available as well, offering a more compact and convenient alternative for couples or solo travelers.
Are there any family house rentals in Pittsfield?
In Pittsfield, Illinois, several family-friendly house rentals can be found, providing a friendly setting for visitors. The town offers a mix of cozy homes, many of which come equipped with spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces for kids to enjoy.

Families can explore local attractions such as the nearby scenic parks and walking trails, superb for outdoor activities and picnicking. The community's charming downtown area features shops and eateries that can enhance the overall experience.
Can I rent a vacation home with a pool or hot tub in Pittsfield?
In Pittsfield, there are several vacation homes available for rent that feature pools and hot tubs. This charming town in Illinois offers a tranquil setting, making it an appealing destination for travelers seeking relaxation. Many of these rentals come equipped with private pools and hot tubs, providing the great backdrop for unwinding after a day of exploration. Travelers can also expect amenities such as spacious living areas, fully equipped kitchens, outdoor seating areas, and sometimes even fire pits for evening gatherings.
Can I find long-stay vacation rentals in Pittsfield?
A long-stay vacation rental in Pittsfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Pittsfield?
In Pittsfield, there are several pet-friendly house rentals available, providing a comfortable stay for travelers with furry companions. These vacation homes typically feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Many properties also include convenient features like laundry facilities and parking, making them ideal for longer stays or family trips. The surrounding area offers opportunities for outdoor activities, with local parks and nature trails that are suitable for walking pets.
Are there any remote work vacation rentals in Pittsfield?
In Pittsfield, Illinois, there are several vacation rentals that cater to remote work needs. Many of these properties are equipped with essential amenities such as Wi-Fi and dedicated workspaces, making it convenient for guests who need to balance work and leisure during their stay. The town itself offers a peaceful atmosphere, great for concentration, while still being close to local parks and small-town charm. Travelers can expect comfortable accommodations that often include fully equipped kitchens, cozy living areas, and outdoor spaces for relaxation after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pittsfield vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pittsfield with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Pittsfield?
In Pittsfield, popular vacation rental amenities include WiFi, kitchens, and kitchen islands, making it easy for guests to prepare meals and stay connected during their stay. Many rentals also feature private pools, offering a refreshing retreat, especially in warmer months. Additionally, travelers can expect balconies in some properties, providing outdoor space to relax and enjoy the surrounding views.
When is the best time to visit Pittsfield for a vacation rental?
The best time to visit Pittsfield for a vacation rental is during the peak summer season, particularly in July. This month brings warm temperatures and a vibrant community atmosphere, great for those looking to indulge in outdoor activities or explore local events. The average temperatures during this time typically range from the mid-70s to low 90s Fahrenheit, providing an excellent backdrop for enjoying the picturesque countryside.

From June to August, Pittsfield buzzes with various tourist activities, including local festivals, outdoor concerts, and recreational opportunities in nearby parks. This lively season attracts families and adventure enthusiasts alike, making it a great time to connect with fellow travelers and engage in community events.

For those seeking a more budget-friendly experience, consider visiting in January. While this is the low season, the colder temperatures ranging from the low 20s to mid-30s Fahrenheit can offer a cozy escape, ideal for enjoying a peaceful retreat in a charming vacation rental. You might find unique winter activities or simply relish the tranquility of a quieter town.

Ultimately, your ideal travel time to Pittsfield will depend on your preferences for lively summer festivities or a serene winter getaway.
How early should I book a Pittsfield vacation rental?
Book your Pittsfield vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pittsfield?
In Pittsfield, visitors can explore several attractions that showcase the area's charm. The historic downtown features quaint shops and local eateries, making it a pleasant area to stroll through. Nearby, the Pike County Courthouse is a popular landmark with beautiful architecture. Outdoor enthusiasts can enjoy the scenic landscapes at nearby parks, including the scenic trails at Lake Pittsfield, which is ideal for fishing, hiking, and picnicking. The local community also hosts various events throughout the year, offering insights into the cultural fabric of the region.
Can I change or cancel my Pittsfield home rental booking on Vrbo?
To find Pittsfield vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Pittsfield vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCareℱ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCareℱ, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCareℱ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCareℱ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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