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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Superhost

An outdoor pavilion is highlighted by a spacious seating area featuring multiple barstools and a dining table. A stone bar is visible, with decorative lighting and local signage. Surrounding lush greenery and seasonal flowers enhance the welcoming atmosphere.

Home in Crawfordsville

4.79 out of 5 average rating, 39 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. Get a taste of farm life with farm animals on property interactions

A modern farmhouse stands on an expansive green lawn, framed by trees in the background. The structure features a large wrap-around porch, with seating visible and a symmetrical, pitched roof. Soft morning light enhances the tranquil setting, inviting exploration of the surrounding 9-acre property.

Home in Crawfordsville

5 out of 5 average rating, 5 reviews

NEW Sugar Creek Farmhouse on 9 acres

**NEW** Enjoy this picturesque, 9-acre setting on Sugar Creek, offering woods to wander, trails to explore, and a wildflower field that’s especially beautiful in the warmer months. You’ll enjoy full use of the house, yard, and surrounding property, where you might see deer, owls, and other wildlife while walking the trails. Mornings along the ridge come with breathtaking sunrises, and the peaceful, remote setting is just minutes from town and close to some of the best hiking trails in Indiana.

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

4.87 out of 5 average rating, 23 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, 3 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, 599 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.

The exterior of the cedar log cabin displays a sloped roof with large windows framed by natural wood. A wraparound porch with planters is visible, surrounded by lush greenery and mature trees. The rustic architecture harmonizes with the forested setting.

Cabin in Waveland

4.8 out of 5 average rating, 79 reviews

*Sugar Creek Cabin w/spa bordering 2 state parks!

Authentic western cedar log cabin surrounded by 6000 acres of old growth forest! The location is spectacular. You can walk off 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 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, commercial cold plunge, relax pool/swim spa and 3 massage chairs.

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

4.96 out of 5 average rating, 55 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, 138 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, 115 reviews

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.

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

4.96 out of 5 average rating, 240 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.

A newly constructed two-story home with a light-colored exterior sits on a lush, green lawn. The front features a welcoming porch with steps leading to the entrance. Large windows are visible, providing ample natural light, while a spacious driveway accommodates parking.

Home in Crawfordsville

5 out of 5 average rating, 4 reviews

(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.

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, 228 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.