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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Bloomington

4.95 out of 5 average rating, 273 reviews

5 Min IU: Private Parking + Sunlit n' Cozy

Guesthouse 2 Miles from IU/Stadiums, Downtown, Parks, Golf, Lake & more! Special Offers: ☞ Early/late check-in/out — $20. Features: ☞ Private parking ☞ Free street parking ☞ Keyless entry ☞ Fast WiFi - 365 Mbps ☞ Fully stocked kitchen and bathroom ☞ Covered deck ☞ Queen memory foam bed ☞ 55" Smart TV, books, games, puzzles ☞ Spacious, hot shower ★ "Very modern and attractive. Comfortable bed and lots of extras. Loved the safe parking, cleanliness and proximity to all things Bloomington.”

Guest favorite

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 237 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

Guest favorite

Guesthouse in Terre Haute

4.96 out of 5 average rating, 181 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.

Guest favorite

Guesthouse in Terre Haute

5 out of 5 average rating, 158 reviews

10th Street Studio

Welcome to 10th Street Studio! This unit is very spacious, clean, quiet and comfortable. It is located on a quiet street in the Collett Park neighborhood, just minutes to Union Hospital, ISU, and downtown. It is a perfect location for traveling nurses and out of town workers as well as overnight guest passing through town, or those visiting family, friends or students. There is no extra cleaning fees and we offer discounts for weekly and monthly stays. I look forward to hosting you!

Guest favorite

Guesthouse in Crawfordsville

5 out of 5 average rating, 109 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.

Guest favorite

Guesthouse in Bloomington

4.96 out of 5 average rating, 201 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.

Guest favorite

Guesthouse in Madison

4.98 out of 5 average rating, 244 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!

Guest favorite

Guesthouse in Jeffersonville

4.87 out of 5 average rating, 197 reviews

The Cottage Next Door

This charming open concept cottage has all the amenities including full kitchen, laundry, one bedroom with in suite full bath, patio, parking, fire pit, WiFi and so much more. You’ll love this place because of the ambiance, privacy, outdoor space, people and location. A lovely space to unwind and relax after a busy day whether it is work or play. We are a short 10/15 minutes drive to Louisville, Ky. Shared driveway, two parking spaces available. We do not allow pets.

Guest favorite

Guesthouse in Shelbyville

4.97 out of 5 average rating, 100 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Guest favorite

Guesthouse in Louisville

4.91 out of 5 average rating, 507 reviews

Cute Carriage House off Frankfort Avenue

Welcome to "The Cute Carriage House at Frankfort Avenue". Experience serenity in a genuine "tiny house” that comfortably accommodates two people. There are several sleeping options that I will mention below. We are located a short block from premier restaurants and shops on Frankfort Avenue in the classy Clifton Neighborhood...and close to Cherokee Park and the cool Bardstown Road. FYI https://www.leoweekly.com/2020/10/the-winners-of-the-2020-readers-choice-awards/

Guest favorite

Guesthouse in Crawfordsville

4.96 out of 5 average rating, 550 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.

Guest favorite

Guesthouse in Petersburg

5 out of 5 average rating, 291 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.