Vacation rentals in Oakford

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!

Private Beach • Lakefront • Kayaks • Sunsets

The Havana Cabana is your home away from home. Take time to breathe and just be by soaking in your surroundings and being with the people that matter most. We strive to provide you with a relaxing atmosphere and great amenities. You will have full access to your own private, sandy beach (directly behind the home) with amazing sunset views and great fishing. We provide 3 adult kayaks, one double and one child (under 150 pounds), and a pedal boat. Great outdoor fire-pit for s’mores and memories.

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!

Opera House Suite 1

Newly constructed guest accommodations on second floor of the historic J.E. Meyer 1888 Opera House. We are located just two blocks from the scenic Illinois River and Havana's Riverfront Park and its walking paths. Your retired from the local newspaper and the Opera House office is below. They liveclose by for after hours contact. The suite includes a full kitchen and groceries are just a block away, or enjoy the neighborhood restaurants and shopping, all in easy walking distance.

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.

Springfield Haven - Charming

Your family will be close to everything when you stay at this centrally located place. This cozy 2-bedroom, 1-bath apartment in Springfield, Illinois, offers hardwood floors, a fully equipped kitchen, and a comfortable living space with a smart TV. It's pet-friendly and near downtown amenities and public transit, perfect for a comfortable, convenient lifestyle. The apartment was fully renovated with new kitchen, bathroom, floors, windows, paint, and everything else.

Sheridan House - Petersburg - est. 1868

Located one block from historic Petersburg's town square, this charming home welcomes you back in time to experience a slower pace of life . Walk the streets that Abraham Lincoln surveyed in 1836 and visit the Menard County Courthouse to see legal documents signed by Lincoln. Visit Petersburg's beautifully restored Broadgauge restaurant and bar, have coffee, yummy pastries or lunch at the Talisman. Close to 1st and 3rd Wine Bar and Hand of Fate Brewing as well.

My Little Bungalow on Monroe Street.

My Little Bungalow on Monroe is a family friendly, stylish bungalow that is a welcoming space in a peaceful Beardstown neighborhood. Only two blocks from the city square, the Bungalow on Monroe is within easy walking distance of several local eateries, and festival events held in the city square. This two bedroom home is has one queen bed, three twin beds and a daybed. A washer and dryer, as well as a second shower are available in the basement.

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.

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!

Lodging on Main ~ Beckman Suite

This large suite is perfect for families or couples traveling together. There are 2 private bedrooms, one with a king bed, the other with a full bed with a twin loft. It has a full bathroom with a shower and tub. It also has an open concept kitchen and living room. The kitchen has a cook top, microwave, refrigerator, and dishwasher. The living room is super comfy with a 65" TV!

Historic Havana Lofts ~ North Bank Loft ~ Downtown

The North Bank Loft features an open floor plan with full kitchen, open living space and a separate queen bedroom. The living area has windows looking out toward Market Street in Havana for beautiful sunset views. The space has been meticulously restored and boasts high twelve foot ceilings, original restored crown molding, exposed brick and original hardwood maple floors.