Holiday rentals with outdoor seating in Madison County

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.

Cozy Beautiful Updated Spacious 1800’s 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

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.

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.

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 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.

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 .