Guesthouse vacation rentals in Southern Indiana

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Southern Indiana

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

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Guest favorite

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 181 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Mar 16 – 23

ﺩ.ﺇ430 per night

Guest favorite

Guesthouse in Terre Haute

4.97 out of 5 average rating, 132 reviews

College Cottage

Centrally located to 3 colleges and 2 hospitals in a peaceful neighborhood, this cozy, open concept studio guesthouse is perfect for a short- or long-term stay. This newly renovated garage apartment to guesthouse requires no steps and features a spacious fenced in area for your pet. Creativity abounds in this uniquely decorated space. It features a king-sized bed as well as queen sized sofa sleeper. The kitchen is well stocked and has a coffee/tea bar for your enjoyment. Pets are welcome.

Apr 2 – 9

ﺩ.ﺇ313 per night

Guest favorite

Guesthouse in Hamilton

4.99 out of 5 average rating, 144 reviews

Peaceful Little Cabin Retreat - escape in nature

Seeking an escape for some peace and quiet? Welcome to The Little Cabin retreat, located on our 50-acre family farm in Ross, Ohio! Let us take you away from the distractions of life to a place where you can soak up nature in a cozy cabin, all within 30 minutes of downtown Cincinnati. You may fish in the lake if you'd like, or take a ride in the paddle boat, or simply enjoy sitting on the porch listening to the birds. Chances are, you may spot wild turkey or whitetail deer scampering by.

Mar 18 – 25

ﺩ.ﺇ614 per night

Guest favorite

Guesthouse in Bloomington

4.96 out of 5 average rating, 187 reviews

Treehouse Retreat With a View of National Forest

This quaint apartment home is about five miles east of Bloomington and the IU Campus on Hwy 446. The property borders Hoosier National Forest and adjoins 8 miles of hiking trails, with just a short trek to Lake Monroe and a mile to Paynetown SRA. The living room has a wall of windows that looks out over the woods. A bright and airy kitchen w/ all major appliances is off of the living room. An interesting bedroom with a dormer and a large bathroom/ laundry room complete the home.

Sep 13 – 20

ﺩ.ﺇ438 per night

Guest favorite

Guesthouse in Madison

4.99 out of 5 average rating, 225 reviews

Mulberry Cottage In The Heart Of Downtown Madison

This quaint studio cottage is located in the heart of Madison, Indiana. The entire building was fully renovated in 2020 and offers a modern luxurious stay in our beautiful historic town. This property features off-street parking, fast private WiFi, and complimentary beverages/snacks. Within walking distance of shopping, restaurants, and all downtown events. Few properties come close to the accessibility that this Madison cottage provides. We look forward to hearing from you!

Jul 15 – 22

ﺩ.ﺇ419 per night

Guest favorite

Guesthouse in Bloomington

4.94 out of 5 average rating, 208 reviews

Cozy Lil' Gem | Near IU/Stadiums | Parking | Clean

Experience the ambiance of my guesthouse above the detached garage. Abundance of natural light, modern décor and calming energy. With a slanted ceiling, queen bed, sofa bed, and full kitchen, cozy comfort awaits. Enjoy the spacious shower, large closet and private parking, entrance and deck. Plus speedyWi-Fi. Just two miles from Downtown, IU, Parks, Golf and more! Early/late check-in/out for $20 with notice. Ask about long-stay discount. Don't miss out—book today!

Aug 25 – Sep 1

ﺩ.ﺇ386 per night

Guest favorite

Guesthouse in Louisville

4.95 out of 5 average rating, 221 reviews

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

Jul 20 – 27

ﺩ.ﺇ262 per night

Guest favorite

Guesthouse in Rockville

4.96 out of 5 average rating, 183 reviews

Hideaway Hollow

This is a fully furnished picturesque Amish-built cabin in beautiful and secluded Parke County, Indiana. The cabin comes complete with all amenities including full bath with shower, queen bed, A/C, dish TV, wifi internet and full kitchen. There is a large deck attached with a beautiful view of the swinging bridge and the woods. Cook out on the deck's gas grill and enjoy cool evenings by the fire pit (wood provided). Enjoy a nap in the shade in the hammock.

May 27 – Jun 3

ﺩ.ﺇ371 per night

Guest favorite

Guesthouse in Louisville

4.97 out of 5 average rating, 112 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

May 22 – 29

ﺩ.ﺇ519 per night

Guest favorite

Guesthouse in Crawfordsville

4.96 out of 5 average rating, 502 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 and 25 minutes to DePauw University. We live on site. We clean the cottage in accordance with the CDC guidelines to ensure your stay is safe. Pets are allowed on a case by case basis. Please contact us to work out any details.

Mar 10 – 17

ﺩ.ﺇ396 per night

Guest favorite

Guesthouse in Petersburg

5.0 out of 5 average rating, 254 reviews

Stones Throw Country Inn - includes breakfast!

Beautiful country setting 3 minutes from the Creation Museum! Breakfast included! Hosts live on property should you need anything during your stay. Gorgeous sunset views! Easy access to I-275 at exit 11 and about 40 min. to Ark Encounter. For winter fun, Perfect North Slopes is only 15 minutes down the road. Downtown Cincinnati - 30 min.; Dayton, OH, Lexington, KY, and Louisville, KY - All approx. 1.5 hour drive.

Mar 29 – Apr 5

ﺩ.ﺇ518 per night

Guest favorite

Guesthouse in Guilford

4.94 out of 5 average rating, 352 reviews

Twisted Creek Farm -Guest Retreat

Twisted Creek Farm is a spacious rural retreat- 2 miles back on a gravel road winding along Tanners Creek. No neighbors, just wildlife & well Mike and I. • Internet/wi-fi. Cell phone coverage limited • Two bedrooms available - One has private bath, second has bath just outside door • Blu-ray/DVD players/Dish Network - bring your favorite movie or view our collection • Please no smoking on premises

Sep 16 – 23

ﺩ.ﺇ320 per night