Vacation rentals in Montgomery County

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Top-rated vacation rentals in Montgomery County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A living room features a soft beige sofa paired with a patterned armchair and a plaid chair. A light fixture stands beside a table, illuminating a vintage fireplace adorned with artwork and decorative items. Neutral walls and a colorful rug add to the calm ambiance.

Home in Crawfordsville

4.88 out of 5 average rating, 24 reviews

Beautiful home in central wooded neighborhood.

Kick back and relax in this tranqui, wooded setting. Walking distance to Wabash College. Short drive to Turkey Run & Shades State Parks, & several local wedding venues. 40 mins to Covered Bridge Fest. The Master, located on 1st floor includes en suite bath. 2 add'l bedrooms share a full bath upstairs. Deer, fox, wiled Turkey and owls are commonly encountered while sitting on the porch, or walking the neighborhood. This is a smoke free, pet free home. Parties are strictly forbidden.

The exterior of the primary house is visible, featuring a wooden facade and large windows. A spacious deck area is seen with lounge chairs and a view of the surrounding trees. The detached bunkhouse is located in the background, offering additional accommodation.

Home in Crawfordsville

5 out of 5 average rating, 4 reviews

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.

Top guest favorite

The living area is furnished with a comfortable brown pull-out sofa and two chairs. A wooden coffee table sits in front, accompanied by a decorative area rug. Natural light enters through a window, with light curtains enhancing the cozy feel of the space.

Guesthouse in Crawfordsville

4.96 out of 5 average rating, 602 reviews

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.

Top guest favorite

A spacious bedroom is furnished with a queen bed covered in a light grey bedding set. Flanking the bed are two bedside tables with lamps, enhancing the soft lighting. A bench sits at the foot of the bed on a plush area rug, and a closet is visible in the background.

Guest suite in Crawfordsville

4.95 out of 5 average rating, 60 reviews

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.

Top guest favorite

An open concept living space featuring a kitchen island with seating and a cozy seating area. Large windows provide ample natural light, with views of the surrounding woods. Warm wood flooring enhances the inviting atmosphere, while a door leads to a private area.

Guesthouse in Crawfordsville

5 out of 5 average rating, 142 reviews

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.

Guest favorite

The tiny home, set among lush greenery, features a green exterior with a welcoming porch. Seating areas are provided outside, surrounded by trees, offering a serene retreat. Soft sunlight filters through the leaves, illuminating the space.

Tiny home in Crawfordsville

5 out of 5 average rating, 119 reviews

Tree Farm • State Parks • Cozy Glamping • 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.

Top guest favorite

An open living space features hardwood floors and original woodwork, highlighted by soft lighting from overhead fixtures. A comfortable gray sofa is adorned with cushions, while a dining area with a wooden table and chairs is visible. Bar stools are arranged near the kitchen counter.

Loft in Waynetown

4.95 out of 5 average rating, 242 reviews

Residences at Knights Hall, Unit A

Newly renovated 1 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.

Guest favorite

A charming exterior of the lodge is featured, showcasing a wooden porch supported by exposed beams. A wedding dress is displayed on a hanger, highlighted against the rustic backdrop. Lush green plants and a decorative bench add to the inviting atmosphere.

Cabin in Crawfordsville

4.95 out of 5 average rating, 233 reviews

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.

Superhost

The exterior of the cabin is shown, featuring a white façade with dark shutters and a turquoise door. A covered porch with seating overlooks the surrounding greenery, while planters with flowers add a touch of color. The ample driveway provides easy access.

Cabin in Crawfordsville

4.69 out of 5 average rating, 36 reviews

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.

Guest favorite

A historic house is surrounded by a spacious green lawn, under a clear blue sky. The two-story structure features a large porch and multiple windows, while mature trees provide shade in the yard. A white fence outlines the property, enhancing its serene setting.

Home in Crawfordsville

4.91 out of 5 average rating, 11 reviews

Monon Manor

*NEW* The whole group will enjoy easy access to everything from this centrally located place. Gorgeous Historic Home near Wabash College, Ironman Raceway and downtown Crawfordsville. Less than 45 min drive to Purdue, DePauw, Turkey Run and Shades State Park. Located 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.

Guest favorite

The exterior of a yurt-style cabin features natural wood siding and a corrugated metal base. Two sets of wooden steps lead to the entrance, framed by large windows. A small outdoor sitting area is visible on a gravel patch, surrounded by lush greenery.

Cabin in Crawfordsville

4.97 out of 5 average rating, 187 reviews

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.

Apartment in Crawfordsville

4.67 out of 5 average rating, 3 reviews

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.