Holiday rentals in Montgomery County

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.

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.

Guest house in Crawfordsville

4.96 out of 5 average rating, 586 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.

Guest suite in Crawfordsville

4.96 out of 5 average rating, 50 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.

Guest house in Crawfordsville

5 out of 5 average rating, 127 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.

Tiny home in Crawfordsville

5 out of 5 average rating, 101 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.

Guest favourite

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.

Guest favourite

Cabin in Crawfordsville

4.96 out of 5 average rating, 220 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.

4.75 out of 5 average rating, 24 reviews

Cabin in Crawfordsville

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 the pontoon boat is available for rent at an additional fee, providing endless opportunities for water activities and exploring the lake.

5 out of 5 average rating, 5 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.

Home in Waveland

4.87 out of 5 average rating, 71 reviews

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.

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.

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Other great holiday rentals in Montgomery County

4.79 out of 5 average rating, 28 reviews

Kids' Room- The Queen & I BnB

AprilRating, 5 stars9 months ago

After staying at Isaac’s place last week due to an unexpected family emergency, I was so impressed that I secured a second stay. I was confident that this stay would be just as perfect; it was that and more. The home was spotless, communication was excellent, easy instructions, and well worth the price of the stay. This will be my go- to Crawfordsville area place to stay. Thank you Isaac and family for your hospitality and kindness.

4.93 out of 5 average rating, 15 reviews

Servants' Quarters

MeganRating, 5 stars7 months ago

Great place to stay! Close to Purdue and Turkey Run. Hosts were great! Very clean and comfortable.

4.98 out of 5 average rating, 41 reviews

The Queen & I Homestead- 5 Beds in 4 Rooms

BeckyRating, 5 stars11 months ago

The Queen and I was so unique with the free range chickens and turkeys. Truly farm-ish. And the house is a gorgeous restoration! The rooms were big enough for our family of 6 to stay. Beds were clean, comfortable, and the bathrooms were convenient and very functional. Everything was as it was described. And the hosts, while on site, were available when needed but not invasive in any way. We loved our weekend there!

4.87 out of 5 average rating, 111 reviews

The Spare Room- The Queen & I B&B

BrandieRating, 5 stars7 months ago

I found the room to be comfortable, very clean, and located close enough to downtown Crawfordsville to be convenient, while still feeling outside of city. I especially loved seeing the chickens and turkeys walking around outside in the morning. Sound does carry pretty easily throughout the house, but I guess that's part of staying in a pretty, historic home.

Guest favourite

4.91 out of 5 average rating, 33 reviews

The Queen's Chamber & Kids' Room

ErikaRating, 5 stars10 months ago

We had a lovely stay with Holly and Isaac. When we arrived just after sunset, the Guinea fowl clucked at us from the trees, setting the tone for our stay in this lovely farmhouse. We were able to easily find our rooms and get in, though Holly also quickly popped out to make sure we had what we needed. The rooms were spacious, with high ceilings, gleaming floors and lovely oriental rugs. We used and loved both the clawfoot tub and the clawfoot shower. My kids (one adult) were comfortable in the kids room, and I took my coffee in the morning while looking out the window at the chickens, turkeys and fowl from our bedroom window. Fun add on: they have a historical painting and photo of the house over its history. Will stay again!