Holiday rentals in Chatham

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Top-rated holiday rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The living room features a comfortable sofa paired with two patterned armchairs, creating a cozy seating area. A light-toned rug anchors the space, while a small coffee table sits centrally. A dining area is visible in the background, illuminated by natural light.
Home in Auburn
5 out of 5 average rating, 46 reviews

The Cottage at Edgewood

Located along the sixth fairway of Edgewood Golf Club and 20 minutes south of Springfield, our State Capital, the Cottage at Edgewood is a newly renovated ranch style, single-family home. Whether you’re visiting family, playing golf, touring the Land of Lincoln sites, or cruising Route 66, the Cottage is convenient for all. Guests have exclusive use of the entire house, with a large yard and walkout patio perfect for enjoying your morning coffee, evening drinks, and waving to golfers passing by.

Top guest favourite
Townhouse in Springfield
4.96 out of 5 average rating, 131 reviews

Project Southtown...a work in progress!

Groups of 9+ ask about a 1 day minimum. 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 25+ adults! Https://Airbnb.com/h/Skateboard1 Https://Airbnb.com/h/Skateboard2 One block off US Route 66!

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, 103 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
Tiny home in Springfield
4.98 out of 5 average rating, 600 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
A cozy living room features a leather sofa adorned with colorful throw pillows, complemented by a vibrant area rug. Natural light filters through large windows, while a stone gas fireplace provides warmth. A 50” TV sits beside eclectic decor, including plants and framed art.
Home in Springfield
5 out of 5 average rating, 68 reviews

Mod Pod: MCM Home w Fireplace, Sauna, & Yard

Launch your memorable stay at Little Mod Pod, a fully remodeled 1951 Mid-Century-Modern tiny home in the heart of Springfield, IL. More spacious than it appears, this vintage gem is tastefully decorated with stylish MCM touches and retro nods to the 1950s – yet with every comfort for restorative rest; a sauna and fireplace are just the beginning. Sitting on a picturesque, landscaped lot with backyard in a quiet, residential neighborhood, Little Mod Pod is the perfect spot for a magical stay.

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, 55 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)

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, 19 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.

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.
Flat in Springfield
4.93 out of 5 average rating, 772 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.

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.
Flat in Springfield
4.94 out of 5 average rating, 376 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.

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
4.93 out of 5 average rating, 175 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
A cozy bedroom is presented with a spacious bed featuring light orange bedding and matching decorative pillows. A small shelf with a plant is mounted beside the bed, while three framed landscape prints adorn the wall above it. A ceiling fan is visible in the corner.
Home in Springfield
4.97 out of 5 average rating, 137 reviews

Sunny 4-bedroom Cottage Fenced Yard

Welcome to the Lincoln Cottage! You'll love the natural wood floors and beautiful morning light that comes through the bay windows. It's centrally located only a mile off the highway but tucked away in a warm and welcoming neighborhood between west side restaurants/shopping and downtown tourist activities. We think it's the perfect location! ** 2-4 minutes to Scheels Complex **

Guest favourite
A cozy living room features a light-colored plush sofa adorned with decorative pillows, positioned in front of a wooden coffee table. Soft string lights create a warm ambiance around a mirror and decorative plants in the background. Natural light filters through sheer curtains.
Home in Springfield
4.94 out of 5 average rating, 389 reviews

Cozy Quiet 2BR/1BA Bungalow | Central Location

Step into a warm, fully furnished Springfield bungalow that’s perfect for families and longer stays. Safe neighborhood for walking. You’re centrally located near restaurants, groceries, and shopping, with downtown attractions and Washington Park just minutes away—plus quick highway access in under 10 minutes.

Popular amenities for Chatham holiday rentals

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