Holiday rentals with outdoor seating in Madison County

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

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!

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.

🦉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!

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.

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.

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.

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.

1800s Farmhouse-Modern Luxury Meets Historic Charm

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.

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 .

7 minutes from Casino | Valley Grove Retreat

Quiet, family-friendly retreat just 7 min from Harrah’s Casino & I-69 with easy private parking. Unwind in the cozy 1-bed suite: comfy bed, sofa sleeper, smart TV, and fast Wi-Fi. A mini-fridge, microwave, and coffee maker keep snacks simple. Perfect for couples or small families seeking peaceful nights and quick casino fun.

Studio M

Studio M is located in the small Historic town of Pendleton, IN. The home is within walking distance of our shops, restaurants and Falls Park. We have a fully stocked kitchen, car port with chairs to sit out and enjoy the beautiful outdoors. Our house is conveniently located to Fishers, Anderson, Noblesville and Indianapolis.