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

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 neighbourhood boasts a charming atmosphere with a variety of local shops and eateries, making it a delightful place to explore on foot. Additionally, it's conveniently located near some of the town's top attractions, such as the historic Pittsfield Courthouse, which showcases beautiful architecture and rich local history. Visitors can also enjoy the nearby scenic parks, great for leisurely strolls or picnics.
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 travelling 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.
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, a variety of vacation rental accommodations are available, with apartments, vacation houses, and cabins being the most popular options. These rentals are scattered throughout the town and offer different experiences depending on travellers' needs. Most apartments come equipped with essential amenities such as fully equipped kitchens, comfortable living areas, and convenient access to local attractions. Vacation houses typically provide more space with multiple bedrooms and outdoor areas, making them suitable for families or larger groups. Cabins, often located in more tranquil settings, offer a rustic charm with the comforts of home.
Are there any family house rentals in Pittsfield?
In Pittsfield, Illinois, there are several family-friendly house rentals available for those looking to enjoy a getaway. This charming town offers a range of properties that cater to families, often featuring spacious living areas, fully equipped kitchens, and outdoor spaces superb for children to play. Many homes also come with amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.
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 or hot tubs. This quaint town offers a relaxing atmosphere, making it an excellent choice for those seeking a peaceful getaway. Many of these properties come equipped with private pools and hot tubs, providing a great setting for unwinding after a day of exploring the surrounding area.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Pittsfield?
In Pittsfield, travellers can find several pet-friendly house rentals that cater to various needs. Many of these properties come equipped with amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces for both guests and their pets to enjoy. The homes often feature comfortable furnishings and updated appliances, ensuring a pleasant stay.
Are there any remote work vacation rentals in Pittsfield?
In Pittsfield, Illinois, there are several remote work vacation rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties offer dedicated workspace options, such as desks or office setups, ensuring a productive environment. Travellers can expect amenities like high-speed Wi-Fi, comfortable seating, and peaceful surroundings, which are essential for remote work. 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 travellers 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 essential kitchen appliances such as dishwashers and microwaves, which enhance convenience for guests looking to prepare their own meals. Additionally, properties often come equipped with coffee makers to ensure a fresh brew is readily available. Many rentals also provide cookware, dishware, and utensils, making it easy for travellers to enjoy home-cooked meals during their stay.
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 season from June to August. This vibrant period is especially popular among families and outdoor enthusiasts, as the warm summer temperatures encourage a host of activities, from hiking in the nearby trails to enjoying picnics in the area's beautiful parks.

July stands out as the most popular month, with its inviting weather typically ranging from the mid-teens to low 30s Celsius. The lively atmosphere during this time draws visitors who are keen to explore the local attractions, attend community events, and relish the long, sunny days superb for outdoor adventures.

If you're looking for a more budget-friendly option, consider visiting in January. During this time, this month offers a unique charm, with opportunities for winter activities and a peaceful retreat from the busier summer months.
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.
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 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 travellers 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 cosy cabin or a beach house, 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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