Vacation rentals with outdoor seating in Madison County

5 out of 5 average rating, 28 reviews

Apartment in Pendleton

Historic Downtown Hideaway

This inviting space is tucked away in the heart of historic downtown Pendleton..You'll find yourself steps from local cuisine, a cozy coffee shop & multiple boutiques offering plenty of opportunities for relaxation & exploration. Only a block to Falls Park & stroll along its walking paths, offering a peaceful retreat for nature lovers. Perfectly nestled between Fishers, Fortville, Noblesville & Anderson for easy exploration of towns & attractions. Easy access to I-69 for shopping & entertainment

A modern living area is furnished with a comfortable gray sofa and an accent chair. A large flat-screen TV is mounted on the wall, while a decorative rug enhances the space. Natural light enters through the windows, illuminating the open layout.

4.98 out of 5 average rating, 84 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!

Guest favorite

A private, fenced patio features a hot tub and two wooden chairs, accompanied by greenery along the side. Warm string lights hang overhead, providing soft illumination in the evening. The ground is paved with smooth concrete, creating a comfortable outdoor space.

4.86 out of 5 average rating, 42 reviews

The Clematis Cottage

Nestled in historic downtown Pendleton, IN, this completely remodeled studio offers the perfect blend of comfort and style. Enjoy a chef-style kitchen, luxury bathroom with a rain shower and radiant heat, and an electric fireplace. Relax in the private, fenced patio with a 4-person hot tub. Features include a queen bed, convertible couch, blackout curtains, vaulted ceilings, and no steps—ideal for accessibility. Walk to local shops, restaurants, and bars, with parking just steps from the door.

4.92 out of 5 average rating, 308 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 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.

4.96 out of 5 average rating, 23 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.

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.

4.74 out of 5 average rating, 38 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.

Guest favorite

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, 16 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.

4.92 out of 5 average rating, 48 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.

Guest favorite

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, 176 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 cozy family room features a leather sofa and armchair, both adorned with black and white checkered throw pillows. A wooden coffee table sits in the center, complemented by a decorative plant. Tall windows allow natural light to brighten the space, accented by soft shades.

5 out of 5 average rating, 24 reviews

Cozy Farmhouse Getaway updated modern comfort

Escape to a cozy, peaceful 1800s farmhouse with modern updates in a quiet rural setting. Enjoy large spacious rooms to relax and enjoy a quiet space. Smart TVs, fast internet, a large fully stocked kitchen, and a coffee bar. All this within 5–15 mins to dining, shopping, parks, entertainment, quaint small towns, a casino/horse/race track, and I-69 for easy access to trips to Indianapolis or Fort Wayne.

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, 136 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.