Family-friendly holiday rentals in Montgomery County

Mimi's Country Cottage

Quaint, quiet and cozy cottage set in a tranquil park like setting with all the amenities of home. Ten minutes to Shades State Park and twenty minutes to Turkey Run State Park. A great place to stay for the Covered Bridge Festival. 15 minutes to Wabash College, 25 minutes to DePauw University, 45 minutes to Purdue. We live on site and our back door is approximately 600 ft. from from the Airbnb. At this time we do not allow pets. We clean the cottage in accordance with CDC guidelines.

Tree Farm • State Parks • Fire Pit

Welcome to your private setting on 60 acres with Christmas trees, woods, and excellent view of Sugar Creek from the back of the property! Connect with nature and solitude. Quiet setting in the trees; conveniently located near •Hiking (Turkey Run - 30 min; Shades State Park - 20 min), •Wabash College (5 min) and Purdue University (35 min), •Canoeing (public launch - 2 min ; Sugar Creek Canoe rental - 4 min). Groceries and dining are just 5 minutes away. Just under an hour to Indy.

The Upper Room

Located in Crawfordsville's downtown historic district. This cozy apartment is four blocks from Wabash College. Eight downtown restaurants and a coffee shop are all within 3-5 blocks. The unit has a spacious bedroom with a queen bed, a living room, and HDTV. It has a private entrance, a small kitchenette, clean bathroom, and street parking. Within easy driving distance to Purdue University, downtown Indy, the annual Covered Bridge Festival in Parke County and Turkey Run State Park.

Red House Guesthouse

Relaxing guesthouse in peaceful country setting with local deer herd visiting frequently. Close to Shades and Turkey Run State Park and Wabash College. Great location for Covered Bridge Festival, and wedding venues. We live on site with our 2 chocolate Labradors. The guesthouse has a private entrance and private outdoor deck facing the woods. Entire living space is handicapped accessible including large bathroom with walk in shower. Cleaning is in accordance with CDC guidelines.

Residences at Knights Hall, Unit B

Newly renovated 2 bedroom loft in a historic building in Waynetown. Large open living space with plenty of space to relax, hardwood floors and original woodwork. This property too unique to describe properly. Waynetown is 1 mile from Interstate 74 for easy overnight access. No traffic, no light - 2 minutes and you can get gas before you get back on the highway. There is a gas station, grocery store, post office and bank all within walking distance of the unit. No smoking or pets.

Townsend Lodge at Hidden Hollow Farm

The lodge is a very private/secluded setting located on 62 wooded acres. Everything nature has to offer is just outside the door. Enjoy the trails, garden ponds, or just relax on the porch and listen to the birds sing all day long. Inside you will find all the comforts of home along with fireplace, cabin decor, and walk-in shower with unlimited hot water. Perfect place for a couples romantic getaway or gatherings for holidays, bachelorette/bachelor party, and more.

Cheerful lakeside cottage with 3 bedrooms, 2 baths

Beautifully remodeled cottage located close to Crawfordsville, Indiana. Minutes to Wabash College. Less than an hour to Indianapolis. Close to both Shades and Turkey Run State parks. Relaxing lake front setting provides opportunities to sit on the dock, swim in the lake, or grill on the back deck. King bedroom, and two queen bedrooms share two full baths, one with a beautiful walk in shower. Newly remodeled kitchen is fully stocked. Washer and dryer available.

Monon Manor

Charming historic home, with easy access to everything from this centrally located charming Historic Home near Wabash College, Ironman Raceway and downtown Crawfordsville. Less than 45 min drive to Purdue, and DePauw, and 25 min to Turkey Run and Shades State Park. Located directly on walking and biking trails. Indoor/outdoor living with fire pit and wildlife. Facing gorgeous western sunset views. Hosts families and friends for large or small gatherings.

Lakefront Cabin

The lakefront two-bedroom one bath cabin is nestled on over an acre, offering stunning views of the sparkling waters and lush greenery surrounding it. The cabin boasts a cozy living area with a wood fireplace. The bathroom features modern fixtures and a shower. Outside, A private dock allows for easy access to the water, and providing endless opportunities for water activities and exploring the lake. Make sure to visit the beach located at the clubhouse.

Cozy Farmhouse on 10 acres across from State Park

Gorgeous location and with picturesque scenery! The property is surrounded by Shades State park and there is the area is known as the covered bridge capital of the US with 33 covered bridges within a 20 minute drive. This home has been fully remodeled with two new baths, a master suite, a large screened porch and new kitchen all on 10 acres. You have the option to visit the Nordic spa at our Log Cabin next door for a discounted daily rate.

Yurt inspired Cabin at The Queen & I Homestead

Yurt meets cabin. Private unique cabin on our homestead set in between native prairie grass and woods, this is the perfect oasis to get away. Inspired by turn-of-the-century charm of our 1873 Italianate Farmhouse, this will be like a vintage treasure rediscovered. Quality craftsmanship with artisan designs to lend character and authenticity, the luxury bathroom with walk-in shower and kitchen will make this stay an unforgettable trip.

Lake Treehouse

Unwind in this serene, stylish retreat with breathtaking lake views and surrounding natural beauty. This brand new studio apartment, completed in 2025, offers the perfect escape. 5 miles from Ironman Motocross racing, 14 miles from Turkey Run, 6 miles from Shades State Park, 20 miles from Covered Bridge Festival, 5 miles from Wabash College & 30 miles from Purdue University.