Vacation rentals in Chatham

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Top-rated vacation rentals in Chatham

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Top guest favourite
The exterior of a charming historic home is displayed, featuring a welcoming porch, a gravel driveway, and well-maintained landscaping. Large trees provide shade, and an American flag is gently waving. A spacious garage is located adjacent to the house.
Farm stay in Springfield
5 out of 5 average rating, 102 reviews

More Than a Place to Stay, It’s An Experience!

Welcome to your one-of-a-kind, historic experience located in the countryside just 1 mile east of Springfield city limits. You will experience our finely furnished family home with modern technology & conveniences, originally the one-room North Round Prairie country school from 1875 to 1945. Deluxe features include nature trails, wildflowers, sitting areas, full garage access, and a working cattle farm provide a one-of-a-kind, quality experience. A 3rd bedroom suite upstairs was added in '22!

Top guest favourite
An inviting interior features a rustic design with wooden accents and a cozy double bed covered in a patterned blanket. A wooden staircase leads to additional sleeping space. A flat-screen TV is mounted on the wall, and details of nature-themed decor can be seen throughout.
Tiny homes in Springfield
4.98 out of 5 average rating, 580 reviews

Tiny Home Cabin - No Cleaning Fee

You won’t forget the peaceful surroundings of this rustic destination. It maybe small at 375 sf, but it has all the features of most hotels with one queen bed and a full bed in the loft. Located near downtown Springfield, IL and many Abraham Lincoln attractions. Deer often walk around the property which is on a quiet dead-end residential street. The kitchen has most everything you need to cook meals. Plenty of towels, soap, shampoo, and extra pillows. Watch Netflix, Hulu, and Disney also.

Top guest favourite
Townhouse in Springfield
4.96 out of 5 average rating, 130 reviews

Project Southtown...a work in progress!

We have character! This hip old loft has seen skating's best, including TONY HAWK TWICE! Thanks to Scheels, we have a NEW batting cage and golf simulator! Bring the whole team, save a ton of money, and be the envy of the tournament. More practice and better rest will put you in the winners circle! By booking the links below, you can sleep up to about 25 adults, before needing the air mattresses! Https://Airbnb.com/h/Skateboard1 Https://Airbnb.com/h/Skateboard2 Please read my reviews!

Top guest favourite
A close-up of a potted plant showcases lush green leaves, adding a touch of nature to the outdoor space. In the background, a cozy seating area with cushioned chairs is visible, along with a light-colored patio wall illuminated by soft lighting.
Home in Springfield
4.96 out of 5 average rating, 51 reviews

Springfield Stunner

Enjoy relaxing at this peaceful and centrally-located place. We have a coffee and tea bar to wake up to in the morning. Bathroom boasts heated toilet seat, dual shower heads with unlimited hot water! When you're ready to explore, we are a short drive away from many destinations! (Route 66 Drive-In Movie Theatre, Scheel's Sporting Goods, Lincoln House, Lincoln Museum, Lincoln Presidential Library, Knight's Action Park, Bunn Golf Course, Springfield Capital, Washington Park Botanical Garden)

Top guest favourite
A serene farmhouse is visible in the background, framed by tall trees and lush greenery. A vibrant display of pink flowers in the foreground adds color to the peaceful outdoor setting, complementing the tranquil atmosphere of the property.
Farm stay in Springfield
5 out of 5 average rating, 17 reviews

Peaceful Farmhouse in Prestigious Neighborhood

Enjoy a stay at this secluded, peaceful farmhouse, nestled in Springfield’s most prestigious neighborhood. With a large open yard and serene surroundings, it’s the perfect retreat for anyone looking for a getaway. Located just minutes from the Capital, the farmhouse offers both tranquility and easy access to nearby shopping and dining, White Oaks Mall, Target, Walmart, Aldi, Starbucks, etc. For golf enthusiasts, the property is right next to the exclusive Panther Creek Country Club.

Top guest favourite
The main living area features exposed red brick walls and large windows that allow natural light. A television is positioned on a stand across from a pair of sofas. A vintage bicycle decoratively hangs on the wall, and a telescope stands nearby, enhancing the space.
Loft in Petersburgh
4.96 out of 5 average rating, 113 reviews

The Flat

A historic mid-1800’s building on the Petersburg Square! Guests will enjoy the entire apartment-loft which includes private Queen bedroom and private bath. The main living area features a full kitchen, dishwasher, 1/2 bath and washer & dryer. Accommodates up to six guests (airbeds, sofa bed pull out). Smoking of any kind (including cigarettes, cigars, vaping, or marijuana) is not permitted inside the space. Failure to follow this policy may result in additional cleaning fees.

Guest favourite
The living room features a mix of vibrant seating options, including a spacious red couch, floral-patterned armchairs, and a coffee table. Natural light enters through the large windows, with sheer curtains framing the view. A decorative fish hangs above a television console, complementing the  wood floor.
Apartment in Springfield
4.93 out of 5 average rating, 761 reviews

The Purple Awning House at Lincoln Park

Charming two bedroom apartment overlooking scenic Lincoln Park. The only person closer to Abe will be Mary. Whether you are traveling solo or as part of a group, the Purple Awning House's spacious bedrooms, comfortable couch and a large inflatable bed (if needed) ensures everyone will have a good night's rest. * Note that this is a main floor apartment with another separate apartment upstairs (different entry). Please smoke outside and do not bring the butts inside.

Guest favourite
A welcoming front porch is enclosed with large windows, allowing natural light to enter. An American flag is displayed prominently, while purple irises and green plants line the porch. Two blue pots add a touch of color to the grassy yard.
Home in Oak Ridge
4.87 out of 5 average rating, 128 reviews

The Perfect Spot

Enjoy a stylish experience at this centrally-located home in the heart of the medical district. I have designed this home specifically to be an Airbnb. It would be ideal for the visiting travel nurse or doctor or someone wanted to see the Lincoln sites. Within 1 mile of the home are two springfield hospitals, the state capital building, Lincoln’s Tomb, the presidential library and museum, grocery stores, coffee shops, restaurants and many other places of business.

Top guest favourite
A comfortable sleeping area featuring a queen-sized bed with a soft blanket, accompanied by a twin bed upon request. A cozy armchair sits nearby, and natural light filters through large windows, illuminating some indoor plants and decorative elements.
Apartment in Historic West Side
4.94 out of 5 average rating, 372 reviews

Full studio apartment by the best Springfield park

Historic home attic converted to a private 3rd floor apartment, featuring private kitchen and bathroom. Located just two blocks from what many would agree is the best park in Springfield, with a pond, a botanical garden, tennis courts, a playground, and nice roads to run, walk, bike, or skate on. We are also very close to downtown as well as other commercial areas. This space is on the 3rd floor with private access from outdoor stairs and keypad entry.

Top guest favourite
A collage of four images showcases the property’s inviting features. The theater room displays plush seating, while the cozy bedroom highlights soft textures and warm colors. The outdoor area reveals a spacious seating arrangement surrounding a fire pit, and the living room is arranged with a comfortable sectional.
Home in Lake Pointe
4.94 out of 5 average rating, 170 reviews

Abe's Hideaway - HOT TUB, Arcade, Theatre, FUN!

Our property is not just a place to stay; it's an experience in itself! Enjoy our hot tub, arcade, & theater room, PLUS unique "hideaways" that let kids (& kids at heart) play hide & seek in a whole new way. Nestled in a tranquil subdivision near Lake Springfield, our spacious haven offers a gateway to the city's vibrant attractions and beyond. With convenient access to I-72 and I-55, you're just moments away from all that Springfield has to offer.

Top guest favourite
Home in Springfield
5 out of 5 average rating, 8 reviews

Oak Tree Haven

Welcome to your Springfield stay! This charming, newly remodeled duplex is nestled in a peaceful west-side neighborhood — just 5 miles from the SCHEELS Sports Park at Legacy Pointe & the State Fairgrounds, 3 miles from the medical district, and 2 miles from great shopping and dining options. PLEASE BOOK for the actual number of guests you plan to have. NO PETS, NO PARTIES OR SMOKING (INCLUDING VAPING) ALLOWED IN THE HOUSE. NO EXCEPTIONS!

Top guest favourite
A single-story home is surrounded by lush greenery, featuring a red front door and vibrant red chairs arranged on the porch. The expansive driveway leads to a covered parking area, with a quaint landscaping accentuated by colorful flowers and greenery.
Cottage in Historic West Side
4.95 out of 5 average rating, 141 reviews

Pohlman Slough

This home is on a very private and quiet lane across the street from Washington Park. Your front yard is Pasfield Park Golf Course in a unique country setting only five minutes from downtown and the State Capitol. Please note that we do not currently allow unauthorized invite parties or gatherings of non-registered guests of any sort. This rule is not meant to preclude HOST pre-authorized visitors such as family and friends.

Popular amenities for Chatham vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Sangamon County
  5. Chatham