Pittsfield Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Pittsfield, Illinois, USA

Guesthouse Sleeps 7 Kitchen Washer Dryer Dishwasher New Queens
10.0 (25 Reviews)
1 Bedroom 6 Guests
Jellystone Park at Pine Lakes
New
60 Bedrooms 92 Guests
Monroe Street Suites
From£80 per night
9.6 (63 Reviews)
1 Bedroom 2 Guests
Green Acres Hotel
From£81 per night
|
9.1 (42 Reviews)
10 Bedrooms 12 Guests
William Watson Hotel
From£66 per night
|
9.2 (359 Reviews)
1 Bedroom 2 Guests
Rodeway Inn Pittsfield
From£48 per night
|
3.9 (16 Reviews)
21 Bedrooms 6 Guests
Green Acres Hotel
From£108 per night
8.8 (146 Reviews)
1 Bedroom 2 Guests
country lodging
From£96 per night
New
20 Bedrooms 2 Guests
Cozy 3 bedroom family friendly home in pike county IL
10.0 (3 Reviews)
3 Bedrooms 9 Guests
Beautiful secluded lodge with a breathtaking view!
10.0 (2 Reviews)
3 Bedrooms 8 Guests
Rodeway Inn Pittsfield
From£49 per night
6.8 (135 Reviews)
1 Bedroom 2 Guests
West Central Lodging
From£60 per night
5.0 (1 Review)
1 Bedroom 2 Guests

About Pittsfield Vacation Rentals

With more than 26 Pittsfield vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Pittsfield.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Pittsfield, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Pittsfield. Places to stay near Pittsfield are 589.23 ft² on average, with prices averaging £232 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Pittsfield with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Pittsfield?

What are the top vacation rentals in Pittsfield?

How many Rentbyowner vacation rentals are available in Pittsfield?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 26 in the Pittsfield area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pittsfield.