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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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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

4.8 out of 5 average rating, 70 reviews

Remodeled rustic Log cabin with Nordic Spa!

KaytlinRating, 5 stars5 months ago

This place was incredible for a quiet weekend get away. The cabin was perfect for just relaxing. Gabriel was always quick to respond when I had any questions and was always very friendly! The cabin was very clean and felt very much like I was at home. Would plan a trip here again!

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

FaithRating, 5 stars1 month ago

We will happily stay here again. We felt at home right away. Snacks and fruit were available, the rooms were very clean, clutter-free, bed and pillows very comfortable, towels fluffy and absorbent! Hosts are quick to respond. Our only problem was finding it and getting - we arrived late at night after having car problems, it was dark and we couldn’t find a house number. Instructions were in different places in the app, and we’re old and were very tired! If it had been daylight, we probably wouldn’t have had any trouble. Jon came out and made sure we got in all right and offered to help us with luggage. We were grateful for his patience!

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, 122 reviews

Red House Guesthouse

KimberlyRating, 5 stars1 week ago

This is my second stay with Deb and it was as clean, peaceful and lovely as the first. There was even a plate of brownies waiting for me, a welcome treat! I felt safe and right at home. I even had a wonderful chat with Deb before I left in the morning when she brought me some fresh coffee. I highly recommend this as a safe, comfortable respite, especially after a long drive! Thank you!!

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, 217 reviews

Residences at Knights Hall, Unit B

YolandaRating, 5 stars3 days ago

This place was great kind of felt like the walls were a little thin, but I also overthink everything. This place made me fall in love with Waynetown and I would definitely book again although I did get quite a bit cold and when I attempted to turn on the heat there was a popping noise that came from the furnace,I think, but really that made no difference because thankfully they had a heater in the closet which kept me pretty toasty at night. Otherwise, this was an amazing stay, The host was the best & very good with communication I would recommend. Also, he allowed me to request a late check out which I most definitely appreciated. Thank you again.

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, 573 reviews

Mimi's Country Cottage

Annette &BenRating, 5 stars2 weeks ago

Our 2nd stay at Mimi's Cottage & it was just as nice this time. Booked our "getaway" to celebrate our birthdays & spend a little time outdoors. Extremely clean, comfortable & all the amenities of home. Communication with our hosts Teri & Dave was easy & very welcomed. Many cute kitties live on the property & you get farm fresh eggs for breakfast. Slightly off the beaten path but close to all the sights to see & experience in Parke County & Turkey Run State Park. We love it! Highly recommended

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

NicholasRating, 5 stars2 weeks ago

Roger was very responsive and flexible with our booking needs. The house was easy to access and a great size for our large group of friends. The property was fairly large and felt private. some nearby walking paths were very nice. we had a great weekend staying here and would definitely stay here again if we ever returned. thanks!

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Popular amenities for Montgomery County vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Montgomery County

A tree-lined path leads through a spacious green lawn, framed by evenly spaced trees. The road is paved and stretches into the distance, inviting exploration of the surrounding rural landscape.

Private room in Crawfordsville

4.87 out of 5 average rating, 111 reviews

The Spare Room- The Queen & I B&B

BrandieRating, 5 stars6 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.

A tree-lined drive leads towards a spacious lawn, showcasing neatly trimmed grass and evenly spaced trees. Sunlight filters through the leaves, creating a serene atmosphere. The path is framed by well-maintained landscaping, guiding visitors towards the welcoming property.

Private room in Crawfordsville

4.93 out of 5 average rating, 15 reviews

Servants' Quarters

MeganRating, 5 stars6 months ago

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

An elegant brick farmhouse showcases its historical architecture amid a lush landscape. A welcoming sign is positioned near the tree-lined driveway, while the peaceful surroundings include green grass and mature trees, providing a serene rural setting.

Private room in Crawfordsville

4.79 out of 5 average rating, 28 reviews

Kids' Room- The Queen & I BnB

AprilRating, 5 stars8 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.

Private room in Crawfordsville

4.98 out of 5 average rating, 41 reviews

The Queen & I Homestead- 5 Beds in 4 Rooms

BeckyRating, 5 stars9 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!

The historic Italianate brick farmhouse is framed by greenery, showcasing its classic architecture. A welcoming sign is placed at the entrance, complemented by a well-maintained driveway leading to the house. Surrounding trees and open space enhance the rural charm of the setting.

Private room in Crawfordsville

4.91 out of 5 average rating, 33 reviews

The Queen's Chamber & Kids' Room

ErikaRating, 5 stars8 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!

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