Holiday rentals with outdoor seating in Montgomery County

Downtown Crawfordsville Peculiar

The whole group will enjoy easy access to everything from this centrally located place. Steps from downtown Crawfordsville, Wabash College, Pike Place, Fusion 54, Arnie's Pizza, Masonic Temple, and Vanity Theater. This home has four bedrooms in which one is occupied by the homeowner. Parking is plentiful in front of forty-seven. Help yourself to a cozy living and dining room shared space. This a great location to access Iron Man Racing, Indy 500, Strawberry Festival, Turkey Run, and Purdue!

Cottage on Lake Holiday

This well appointed, nicely finished, heated & cooled, home on Lake Holiday is a great place to get away. Only 15 minutes to Shades State Park & 20 minutes to Turkey Run. In the primary house is a queen bed, air mattress, & 2 full bathrooms. The bunkhouse has 2 queen beds. Please note bunkhouse is detached from the primary house. Guests will have to briefly walk outside to access a bathroom. The outdoor shower is not operable October through April. Lake access is not available for guests.

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.

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.

Tree Farm - State Parks -Cozy & Private - 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 •Canoeing (public launch - 2 min ; Sugar Creek Canoe rental - 4 min) •Hiking (Turkey Run - 30 min; Shades State Park - 20 min), •Wabash College (5 min) and Purdue University (35 min). Groceries and dining are just 5 minutes away. Just under an hour to Indy.

(Popular) 5 bed, 3.5 bath - Country Oasis

HUGE, brand new 5 bedroom, 3.5 bath home perfectly situated across the street from the IRONMAN/MXON USA raceway. The Crawfordsville Country Oasis is in an ideal location for you to bring family & friends to stay in style on a 1-acre lot with ample amenities. Our home rests in a peaceful, new neighborhood with ample space for parking and outdoor activities. Enjoy stunning country sunsets while remaining within a 5-10 min drive to plenty of retail and dining options.

Eclectic Creekside Cottage

Cozy up in our eclectic creekside cottage located just outside of the Darlington and Crawfordsville area. Far enough away from the hustle and bustle of downtown life, but close enough for a dinner date if home cooking isn’t on the agenda. Step right outside onto our back patio that includes sitting areas with a full creek view. Experience the creek with our provided kayaks and water tubes. End your night with a relaxing dip in the hot tub.

Vintage Reflections B&B

Historic Victorian home, situated in a quaint town, is tastefully designed with a perfect mixture of nostalgic antiques and functional furnishings. Built c1880 featuring open porches, beautiful ornate woodwork, stain glass windows, & an inground pool. Rent by the room, or the entire house. Great for couples, girls weekend, solo adventures, guys getaway, business travelers, families, wedding parties, and big groups.

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.