Holiday rentals in Pleasant Plains

4.98 out of 5 average rating, 463 reviews

Tiny home in Springfield

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 street. The kitchen has most everything you need to cook meals. Plenty of towels, soap, shampoo, and extra pillows too. Also watch Netflix, Hulu, Prime, and Disney.

4.84 out of 5 average rating, 236 reviews

Home in Pittsfield

Florence Guest House

This 1,200 sq. ft. PRIVATE BOOK is a 175 year old building that Abe Lincoln stayed in. Central A/C, Forced air heat, Two decks (one overlooking the Illinois River), burn pit, outside grill, fully equipped kitchen, screened in porch, ample parking, access to the Illinois River/ boat ramp near, tie up on Our Private Lots! NOTE: RECENTLY HAD Guests' wanting to "JUST GET AWAY" for A Time!!! WE'RE HERE, IF YOU NEED YOUR PRIVATE TIME ALONE, AS WELL!!! ***NEW KEURIG; BRING YOUR K-CUPS!!!***

Guest suite in Springfield

4.84 out of 5 average rating, 140 reviews

Modern Central location 1B1B Suite near Downtown

This historic home has the charm of the old house with the new Modern style set up. It is 3 mins drive from downtown Springfield. Within 5 mins drive to the medical district and the historical sites. This basement unit offers a full-sized memory foam mattress with a private bathroom. 55” TV. A dedicated work space, a romantic dining area. It has microwave, coffee machine,toaster and portable stove,front-load Samsung washer & dryer. (Washer & dryer are shared with main floor unit guests!)

4.94 out of 5 average rating, 165 reviews

Loft in Virginia

Two Doors Down Loft, Virginia-Lincoln territory!

Located in VIRGINIA, IL-Our fantastic, urban vibed loft sits on the town square across from the town's historical courthouse. We are 30 minutes from Springfield, 15 minutes from Jacksonville and in the middle of Abe Lincoln territory and historical markers. The loft is also surrounded by lovely wineries and wildlife parks. Be sure to thoroughly read our listing to ensure that we'll meet all of your needs in exploring our unique area. Two Doors Down is a hidden gem listed at a super price!

4.98 out of 5 average rating, 306 reviews

Townhouse in Murrayville

Peace on the Prairie Too - Tiny House

Need a break from Politics? Peace on the Prairie accepts all guests for who they are rather than what some might wish them to be. Whether it’s a business trip, romantic time together with your significant other, a family vacation, a girl's time away, a secluded spot to work on your music, writing, art, star gazing, or a reconnection with nature, you'll find your inspiration and renewal in this natural rural setting of 23 acres of restored prairie, timber, and wetlands?

4.97 out of 5 average rating, 340 reviews

Cabin in Jacksonville

Bunkhouse Seventy-Four

Once used by seasonal farm labor in the 1930s, Bunkhouse Seventy-Four is a fully restored historic bunkhouse with all the modern amenities for a comfortable getaway. Perfect for couples, it features a full kitchen, bath, queen bed, a spacious porch, beautiful antique stained glass windows, a private outdoor soaking tub (Apr-Nov) on a 7 acre hobby farm. Also check out our listing, Audrey’s Abode, which is next door. Pets are welcome but we charge a $25 pet cleaning fee.

4.93 out of 5 average rating, 695 reviews

Flat in Springfield

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 apartment upstairs. They have separate entrances and there is no shared space or ventilation.

4.95 out of 5 average rating, 285 reviews

Flat in Springfield

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.

4.96 out of 5 average rating, 184 reviews

Home in Petersburgh

The Petersburg Place nestled near downtown

Please enjoy your stay at The Petersburg Place, a cozy 2-bedroom, 1 bathroom home nestled on a neighborhood hillside near downtown Petersburg, Illinois! The house has only three steps required to enter the single-level home, keyless entry, plenty of room to park several vehicles or a boat, a fenced backyard with a deck, full kitchen with cooking essentials, a 55" TV (Amazon Firestick), and Wi-Fi.

Place to stay in Virginia

4.99 out of 5 average rating, 326 reviews

Virginia Lake Getaway/Fishing/Hot Tub/Hammock

Welcome to your charming log cabin located in Virginia, IL. This 1-bedroom, 1-bathroom cabin is designed to provide you with rustic comfort, making your stay truly exceptional. Nestled on a bluff overlooking the serene Virginia Lake, this 1850's log cabin combines historic charm with modern luxuries. Set on 80acres of timber and water for you to explore. Hike, kayak, fish or just relax and enjoy!

5 out of 5 average rating, 309 reviews

Home in Beardstown

The Little White House by the River

Beardstown's original Airbnb location, our home is called the Little White House by the River, and offers a quiet place to stay that is literally a stone's throw (if you've got a decent arm) from the back waters of the Illinois and Sangamon Rivers. DUE TO MAJOR PLANNED RENOVATIONS, THIS LOCATION WILL NOT BE AVAILABLE AFTER SEPTEMBER 30. 2025.

4.95 out of 5 average rating, 415 reviews

Loft in Petersburgh

The Loft on the Square in Petersburg

A beautifully renovated second story loft apartment located on the square in historic Petersburg. The space offers an abundance of natural light with large windows that overlook the historic 1896 Menard County Courthouse and town square. The loft features a mix of charming character and modern amenities.

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Popular amenities for Pleasant Plains holiday rentals

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Other great holiday rentals in Pleasant Plains

4.89 out of 5 average rating, 28 reviews

Home in Havana

McCarthy Lake Cottage

PavelRating, 5 stars3 weeks ago

The view over the lake is priceless.

4.81 out of 5 average rating, 117 reviews

Cheerful 2-Bedroom Home w/ Pet-Friendly Back Yard

JamesRating, 5 stars1 week ago

Nice place, quiet neighborhood, Zachary was very responsive and prompt in returning inquiries. Highly recommend.

Superhost

Cottage in Havana

4.86 out of 5 average rating, 44 reviews

Cozy 2 bedroom cottage with amazing lake view

SuzieRating, 5 stars3 weeks ago

This is the perfect place to relax! The view is gorgeous and it’s a quiet area. Everything was as it appeared in pictures.

Guest house in Springfield

4.74 out of 5 average rating, 285 reviews

Charming Cottage Close to Downtown.

SteveRating, 5 stars1 month ago

It was a short stay, but the place well well equipped, the bed was comfortable and the place was larger than what I had imagined. Larry was very responsive when I did have questions. Getting in and out was very easy. A smooth, no hassle stay!

4.83 out of 5 average rating, 12 reviews

Prime location, clean & pet friendly 3bed house

ShaniceRating, 5 stars2 weeks ago

Really extravagant stay . Me &’ my boys visited from Texas. Very unique & cozy . Will highly recommend for family vacation spot with all amenities. Host was very sweet.

5 out of 5 average rating, 26 reviews

Tiny Gem: MCM Home w Fireplace, Sauna, & Yard

Barry And JaneRating, 5 stars2 weeks ago

By far the coolest airbnb in which I have had the privilege of staying. Small, but so efficient, and masterfully appointed by a talented designer. Exquisite beds and pillows, lovely bathroom, drinks and snacks at the ready and 99 % comped (unless you wanted more than 1 bottle of the several bottles if wine on site - and even then, only 10 bucks). Easy parking. Darling neighborhood. As a woman, I felt so safe there! We even had the pleasure of meeting our host at her beautiful store nearby, which I highly recommend visiting. I already booked another stay. Highly, highly recommended !

4.97 out of 5 average rating, 143 reviews

Home in Elkhart

Relaxing Vineyard Cottage on a Peaceful Farm

SteveRating, 5 stars2 weeks ago

Nice location. Clean and comfortable place to stay. Very nice deck to sit and enjoy the fireflies. Centrally located for our needs.