Vacation rentals with outdoor seating in Madison County

A single-story brick home is presented, featuring a neatly manicured front yard with lush green grass. A concrete driveway is visible, along with a garage on the left side. Two decorative shrubs are positioned near the entrance, which is adorned with a hanging planter.

4.97 out of 5 average rating, 62 reviews

Smart Condo Near Harrah's Casino

Looking for a place to stay that's smart, convenient, and near all the action? Look no further than this Airbnb! This condo is the perfect spot for those who want to be close to the casino, shopping, and everything in between Indianapolis and Muncie. And with all the amenities of home, you'll feel comfortable and relaxed during your stay. So why settle for a boring hotel room when you can have a smart and stylish condo all to yourself? Book your stay today and experience the best of both worlds!

A charming two-story home is surrounded by a well-kept yard. The exterior features a combination of white siding and dark roofing. A stone birdbath is situated in the foreground, while windows framed in white provide ample natural light to the interior spaces.

Home in Alexandria

4.86 out of 5 average rating, 7 reviews

Historic Alexandria Home w/ Private Yard!

Escape the hustle and bustle of Indianapolis and retreat to this 3-bedroom, 1-bath Alexandria vacation rental! Featuring antique decor, a well-equipped kitchen, and in-unit laundry, this property allows guests to step back in time while maintaining comfort and convenience. Visit local sites like the World’s Largest Ball of Paint or The James Dean Museum! Seeking outdoor recreation? Explore Rangeline Nature Preserve. Wind down back home with a drink in the sunroom and rest for your days to come.

5 out of 5 average rating, 19 reviews

A Relaxation Retreat - Cozy spacious farmhouse

If you and your guest want to experience a cozy–serene–relaxing–quiet-peaceful getaway in a beautiful updated 1800's spacious farmhouse in a rural quiet neighborhood...this is the place. Internet & Smart TV's throughout, a large fully stocked kitchen with a coffee bar. The farmhouse is an easy 5–15 minutes' drive to restaurants, coffee shops, fuel, casino, horse track, racetrack, parks, recreation, entertainment, shopping, quaint small towns, and I 69 which leads to Indianapolis or Ft Wayne.

4.91 out of 5 average rating, 291 reviews

The living area features a comfortable sofa and two wicker chairs, complemented by a coffee table on a soft area rug with leaf patterns. A Roku TV is positioned on a wooden console, while a decorative wall feature holds potted plants for a touch of nature.

Guest suite in Anderson

🦉Wooded Suite Retreat - 2BR Easy i69 Access!

Recharge surrounded by nature in this cozy, comfortable, clean 2 BR “in-law” suite nestled among towering ash trees in a rural, wooded neighborhood just outside town near the White River. Enjoy the full private apt (2 BR, LR, kitchen, bath, washer & dryer) on lower level of host’s home. Great for singles, couples, families or work travelers. Near I-69, Anderson University, Hoosier Park, Mounds State Park, Rangeline Nature Preserve, Anderson Airport, St Vincent & Community Hospitals & more!

A cozy living area features a dark green sectional sofa adorned with decorative cushions. A light wooden coffee table sits centered on a patterned rug, while a ceiling fan provides ventilation. Natural light enters through windows, enhancing the inviting ambiance.

4.76 out of 5 average rating, 21 reviews

Pendleton Getaway

Welcome to Pendleton's enchanting getaway—a charming, character-filled sanctuary perfect for a cozy winter retreat. This delightful, historic home features a vibrant kitchen and bathroom with custom cabinets, adding a fun and unique touch to your stay. Each bedroom offers its own magical charm for ultimate relaxation. Located just down the street from historic Falls Park and a short drive to Indianapolis' top attractions, this home is an ideal escape for making winter memories together.

A charming blue home features a well-maintained front yard with green grass and a stone pathway leading to the entrance. Two rocking chairs are positioned on the covered porch, offering a welcoming spot to relax. Large windows provide ample natural light.

4.94 out of 5 average rating, 18 reviews

Super Charming Modern Cottage

Downtown Historic Pendleton. Rich with character and comfy cozy. Open floorplan with lots of room for gathering with family and friends. Each bedroom has TV and comfortable beds with fine linens. The kitchen is well equipped for all your cooking needs. Front covered porch and large backyard with deck. Nestled in a quiet neighborhood. Walking distance to restaurants, coffee houses, antique shops, and Fall Creek Park with hiking trails, gentle waterfalls, and pristine gardens.

Superhost

A two-story house is set in a green landscape, featuring a gabled roof and brick details. A porch with seating is visible, surrounded by well-maintained flower beds and shrubs. The blue sky enhances the inviting curb appeal of the home.

4.72 out of 5 average rating, 32 reviews

Brass Elephant on Taylor

@ the Brass Elephant on Taylor. A peaceful centrally-located home. You'll find everything you're looking for including 3 bedrooms w/ linens (1-King 1-Queen 2 Twin beds) 2 fully stocked bathrooms, kitchen with every utensil/tool you'll need & full laundry room, a great porch/yard to enjoy coffee or wine in the evenings. Pendleton is quiet, historic & you are within walking distance to downtown shoppes & restaurants. Located near shopping, concerts & downtown Indianapolis.

The modern two-story house features a white exterior with large windows and a welcoming entrance. A nearby building displays bright mural artwork. Green lawns surround the property, complemented by manicured bushes, under a partly cloudy sky.

5 out of 5 average rating, 13 reviews

The Little Gray House!

The Little Gray House is a brand new additional to our beautiful private park in Anderson, Indiana! Whether you are traveling for pleasure or business, hosting a private event or just need a weekend getaway...The Little Gray is the perfect place for your stay! Everything in this amazing home is completely brand new. The house will accommodate up to 8 guests. Our property is available to rent to adults 25 years of age or older. No pets or smoking are permitted.

Superhost

The exterior of the historic home is showcased, featuring a vibrant blue facade with white trim. A front porch is visible, supported by white columns. The neatly landscaped area includes newly planted shrubs and a pathway leading to the entrance.

4.93 out of 5 average rating, 44 reviews

The Cozy Cottage - plenty of privacy & work space

The whole group will enjoy easy access to everything from this centrally located place. If you're here for business, you are close to downtown, Hospitals, University and many Businesses. Also, plenty to do with shopping, antique stores for treasures, restaurants, we even have a casino. You are also within 20 mins or so from Muncie Indiana, home of Ball State University and if you head south the other way, you are 30 mins to Indianapolis.

Superhost

A historic house built in the 1890s stands prominently with a yellow exterior and dark blue shutters. The structure features a spacious porch with decorative columns and steps leading up to the door. Surrounding landscaping includes neatly trimmed shrubs and mature trees.

Loft in Anderson

4.93 out of 5 average rating, 162 reviews

The Loft-- Boutique Guest House

Beautifully restored house in the historical district near downtown Anderson. 5-10 walk to downtown restaurants, bars and art museum. 5–10-minute drive to grocery stores and shopping center. Newly furnished and decorated just for Airbnb guests. Fully stocked kitchen, fast Wifi and washer/dryer good for long stays or just a weekend away for relaxing. * This unit is the whole second story of a triplex building.

A charming exterior view showcases a white brick structure with a spacious porch, flanked by lush greenery and colorful flowerbeds. Two sets of large windows provide natural light to the inviting entryway, framed by decorative plants and wrought iron fencing.

4.99 out of 5 average rating, 124 reviews

Historic Eighth Guest house

You'll have a great time at this comfortable place to stay. The unit is set up similar to a duplex . Shared stairway to upper unit with lockbox entry to unit . 2 bedrooms , 1 bathroom, kitchen, sunroom, family room, dining room, laundry room. Adults only in this unit due to balconies . Owner also currently hosts Historic Eighth carriage house .

A spacious studio features a comfortable bed with a light-colored headboard, accompanied by a cozy seating area with a chair and couch. Natural light illuminates the room, and a decorative rug is placed on the floor. Wall-mounted lamps provide additional lighting.