Holiday rentals in Dawson

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!

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!

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.

Big Oak Hillside Retreat, Secluded Tiny Cabin

Escape to the country in this bright and cozy semi off-grid tiny cabin, nestled on a secluded, wooded hillside on our 110-acre farm. This nature getaway features a modern farmhouse interior with rustic accents. Take a moment to unwind on the front porch in comfortable Amish crafted Adirondack chairs. Put a record on and sip a glass of wine as you enjoy the sunset. Perfect for a couple or individual seeking to connect with nature, this rural pet-friendly retreat is the ideal tranquil getaway.

Relaxing Vineyard Cottage on a Peaceful Farm

Discover the charm of our beautifully restored cottage, once the caretaker's home on the historic farm in Elkhart, IL. Ideal for retreats, vacation rentals, or photoshoots, this getaway offers a unique blend of history and comfort. The cottage features three spacious bedrooms, two full baths, and a fully equipped kitchen with an on-site washer and dryer. Unwind on the inviting front porch, where you can soak in the serene views of this tranquil oasis. Book now for a one-of-a-kind destination!

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

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.

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.

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.

Large Updated Historic Beauty

Pet-friendly, large home near the hospitals, downtown shopping, and Lincoln sites! Boasts 5 bedrooms, 2.5 bathrooms, and large privacy fenced yard. This house can sleep 12 people. The master bedroom is a wonderful, relaxing oasis with a large soaking tub in a huge “wet room” with a shower. On the 3rd floor is a video game room with a PS4 and multiple games. Bring your pets and whole family to enjoy this beautifully updated historic home!

Cozy Private Wooded Getaway | Hot Tub | Fire Pit

Welcome to Hidden Grove, a "Beyond the Path" vacation retreat where your experience comes first. This serene, luxury escape sits on 2 private wooded acres just 10 minutes south of Bloomington, IL—soak in the hot tub under the stars, sway in the hammock with a good book, toast s’mores by the fire, then head out for nearby hiking, outdoor adventures, and charming local restaurants and entertainment for a truly rejuvenating getaway.

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.