Holiday houses in Bloomington

Cozy Home with LOTS of space -1 mile to ISU & IWU

Cozy home with Plenty of Space for a relaxing getaway, business trip or family & friend events! Fenced in yard, 1/2 mile from uptown for shopping and dining, 1/2 mile from the Constitution Trail. Location, comfort & space are guest favorites 😊 Host birthdays, graduations, wedding showers, or holiday gatherings in comfort and privacy. If more space is needed for larger groups, the home immediately next door to this one also sleeps 10 and may be available, message me on this if needed!

East St home close to Dtown and Universities

Welcome to your home away from home! This freshly remodeled 2 bedroom 1 bath retreat blends stylish comfort with functionality. Step into an open concept living space featuring a fully equipped kitchen, in unit washer/dryer and all the modern touches you need for a seamless stay. Relax indoors or step outside to enjoy in the private backyard, complete with new patio, and spacious front deck. Whether you are here for work or play this peaceful escape has everything you need to feel at home.

FRONT PAGE: A Book-Lover’s Retreat

Located on Front Street in Bloomington, Illinois, the “FRONT PAGE” is the perfect place to cozy up with a good book and enjoy the perks of a historic neighborhood near Downtown Bloomington. We are book lovers! We outfitted the home with tons of books and reading-related decor for you to enjoy, too! Whether you need a place for the weekend or a long-term stay in Bloomington-Normal, we hope and expect you will enjoy the charm, historical feel, and literary comforts of our bookish home.

2 bed rooms,1 full bath, Well furnished

2 bedrooms, 1 bath home , close to City offices , Statefarm offices, ISU & Wesleyan Universities, Country companies , Ferraro and Rivian Plants in Bloomington Normal area. Right next to a city park, convenient for a relaxed evening walk. The park has a play area for kids. Close to many of the area's best restaurants including a Thai cuisine within couple minutes drive. Walkable distance to public Library and also very close to the downtown area. Coffee machine available for guest usage.

Chic Retreat Small Town Charm, City Sophistication

The ultimate escape, at Wells on Main Guesthouse & Gatherings where small-town charm meets big-city sophistication. Whether it’s a romantic getaway, girls’ weekend, or just time to recharge, our elegant retreat has you covered. Couples can cozy up in dreamy spaces and create lasting memories. Gather your best friends for laughter, wine, and chic relaxation in a stylish setting. With local charm and upscale comfort, every moment feels magical. Book a week long stay and receive 40% off ❤️

Post Office Suite

Historic post office converted to breathtaking guest suite. This Airbnb unit, the Post Office, is located upstairs on the north wing of Central Estate. It comes equipped with a full bath, bedroom, and kitchenette/living room with smart TV. Tall windows, exposed brick, and lovely views of the walking trails will greet you upon arrival. Due to the nature of this old gem guests might see brick debris on occasion. Romance packages available! Luxury florals, wine, desserts $55/$35/$25.

Bed & Bath, 4K 65” TV, Kitchenette Apt (3B)

Step into a quiet, refined private suite designed for comfort and relaxation. This elegant space features a plush queen bed, a spa-style bathroom, and a 65 inch 4K TV for an exceptional viewing experience. The upscale kitchenette includes a microwave, coffee maker, and mini fridge, ideal for light meals and easy mornings. A washer and dryer are available for convenience. The space is intentionally quiet, perfect for rest or remote work, with streaming services available upon request.

The Bailey House

Welcome to The Bailey House! This house is inspired by The Old Grandville House in the classic 1946 movie It's a Wonderful Life. The entry way with its unique style will have you celebrate your arrival to a peaceful house filled with hope, health and cheer. George and Mary Bailey's love story is our love story too. Our vision was to create a space to enjoy all the good things in life which are sometimes the small things. IT'S A WONDERFUL LIFE BECAUSE YOU ARE HERE!

The Courthouse Loft-History, hot tub, and coffee!

The Courthouse Loft resides in the historic courthouse used in the mid 1900s on the second floor of The City House. The original railing and gate of courtroom divides the 825 soft studio style layout. Loft has a separated bath and laundry and a patio with hot tub! Mid century and historic style will wrap you in comfort and luxury during your stay. We are above a coffee shop, so pop downstairs for breakfast and your morning brew! Oh, and never a cleaning fee!

Stylish 2BR Charmer Close to Everything

Stylish, comfortable and close to everything, the whole family is welcome to this 2 bed 1.5 bath restored 1936 home. Down the street from Uptown Normal, 5 mins to ISU main campus, 5 mins to downtown Bloomington, the space is perfect for a quick or long term stay. Fully fenced in yard for your pets, children’s playroom with pack n play, and all the essential amenities you need. Must be ok with older homes as she has quirks like squeaky floors and sticky doors.

The MidCity Loft | Downtown Bloomington

Walk to Grossinger Motors arena, Castle Theatre & Bloomington Center for Performing Arts! Cozy, modern loft in the heart of downtown Bloomington, steps from restaurants, coffee shops, bars, and events. Park once and walk everywhere. Located in a quiet, secure building, it offers a calm retreat after games, concerts, or work. Ideal for weekend getaways or business trips, this space blends downtown convenience with comfort.

Redbird Cottage

Your family will be close to everything when you stay at this centrally located place. Located just a stone's throw away from the prestigious Illinois State University and Illinois Wesleyan University, this charming 3-bedroom Airbnb is the epitome of convenience and comfort. Nestled in a quiet neighborhood, the real gem of this rental lies in its spacious loft area, adding an extra touch of luxury to your stay.