Vacation rentals in Montgomery County

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Top-rated vacation rentals in Montgomery County

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The exterior of a modern, two-story home is showcased, featuring a welcoming front porch with white rocking chairs. Large windows reflect the evening light, while a neatly landscaped area includes flowers and a well-maintained lawn, set against a clear blue sky.

Home in Crawfordsville

New place to stay

5 bed 3.5 bath MXON USA Paradise

This huge, brand new 5 bedroom 3.5 bath home is perfectly situated directly across the street from MXON USA. Bring your family and friends to stay in style on a 1 acre lot in the country with all the amenities you could ever ask for. This home is located in a peaceful, brand new neighborhood with ample space for parking and an included golf cart, making it easy to quickly go back and forth to MXON USA. Enjoy stunning country sunsets while remaining within a 5 minute drive to retail and dinning.

Guest favorite

An outdoor kitchen pavilion is featured, showcasing a spacious dining area with a large table surrounded by comfortable chairs. A bar area is visible, accented by bright red stools. The pavilion is framed by wooden beams and offers an inviting space for outdoor dining.

Home in Crawfordsville

4.86 out of 5 average rating, 29 reviews

Acres of serenity

The comfort of this 5bdrm, 3.5bath ranch are enough to earn a spot at the top of your list. The large kitchen features granite counters & double refrigerators. A 9ft island with granite counters. The master bedroom has a his/hers bathroom. A 3tier commercial style fountain makes for a stylish welcome. The yard features outdoor kitchen pavilion, with a shower curtain waterfall, a wood burn fireplace & a path to a fire-pit area. On the back patio from the master bedroom is private jacuzzi.

A gravel driveway gently curves through wooded surroundings, leading to a rustic log cabin nestled among trees. The cabin features large windows that bring in natural light, and the area is covered with fallen leaves and fresh greens, indicating a serene and tranquil setting.

Cabin in Waveland

4.81 out of 5 average rating, 72 reviews

Remodeled rustic Log cabin with Nordic Spa!

Authentic western cedar log cabin surrounded by 6000 acres of old growth forest! The location is spectacular. You can walk right off of the driveway into Shades State Park and Pine Hills Nature Preserve or take a 10 minute drive to Turkey Run State Park! The area is known as the covered bridge capital of the US with 33 covered bridges within a 20 minute drive. There is a Nordic Spa on site that includes unlimited use of the Saunas, Hot tub, Cold plunge, relax pool and the massage chairs.

Top guest favorite

The bathroom features a modern vanity with a clean white countertop and under-sink storage. A backlit mirror is mounted above the sink, providing ample lighting. A toilet is positioned adjacent to the vanity, and a framed decorative sign hangs on the wall, all set against a soft blue backdrop.

Guest suite in Crawfordsville

4.96 out of 5 average rating, 46 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

A charming greenhouse features large glass windows and multiple doors, allowing ample natural light. The entrance is adorned with seasonal pumpkins and decorative wreaths. Surrounding greenery complements the tranquil rural setting at dusk.

Guesthouse in Crawfordsville

5 out of 5 average rating, 123 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.

Top 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, 96 reviews

Christmas Tree Farm | State Parks | Cozy & Private

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.

Guest favorite

A contemporary kitchen features dark cabinetry and grey textured countertops. Stainless steel appliances, including a refrigerator and microwave, are present. A double sink is positioned in front of the counter, with additional storage shelves displaying decorative items above.

Loft in Waynetown

4.92 out of 5 average rating, 218 reviews

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.

An open-concept living area features plush, light-colored sofas adorned with decorative pillows. A glass coffee table sits centrally among the seating, reflecting the natural light from large windows. The view overlooks a cozy loft space above, enhancing the spacious atmosphere.

Loft in Crawfordsville

4.72 out of 5 average rating, 18 reviews

20% Off Luxury Downtown Business Creative Space

Welcome to The Lions Den | Designed by Jeremiah & Co. This is a unique and creative space in a Mid West location with access to travel, entertainment, food and the family experience that you have been searching for. The Lion’s Den is a newly renovated office/studio space located in the heart of central Indiana, in the city of Crawfordsville. This space is a largely open concept design with high ceilings and open space for your relaxation, inspiration or gathering.

Guest favorite

A serene lake view is presented, featuring calm waters reflecting fluffy clouds and greenery. A wooden dock extends into the lake, with striped lounge chairs positioned for relaxation. Lush trees line the shore, enhancing the tranquil ambiance of the surroundings.

Cottage in Crawfordsville

4.84 out of 5 average rating, 68 reviews

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.

Top guest favorite

An outdoor patio area is presented, featuring four chairs positioned around a colorful rug. A wooden deck is surrounded by a lattice fence, while green trees and grass provide a natural backdrop, creating a serene and inviting space for relaxation.

Guesthouse in Crawfordsville

4.96 out of 5 average rating, 574 reviews

Mimi's Country Cottage

Quaint, quiet and cozy cottage set in a tranquil park like setting with all the amenities of home. Close to Shades and Turkey Run State Parks. 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. PETS ARE NOT ALLOWED. We clean the cottage in accordance with CDC guidelines.

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

5 out of 5 average rating, 3 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.

A cozy bedroom features a spacious bed with layered bedding and accent pillows. Large windows allow natural light to fill the room, with double doors leading to an outdoor deck. Textured walls and decorative elements add to the inviting ambiance.

Home in Crawfordsville

4.8 out of 5 average rating, 10 reviews

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.