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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Top guest favorite

A cozy living area is highlighted by a three-bulb brass chandelier above a tan sofa, complemented by a wooden table. The wall features an arrangement of framed mirrors in gold and silver tones, while a doorway leads to other areas of the carriage house.

Guesthouse in Indianapolis

4.99 out of 5 average rating, 241 reviews

Charming Meridian Kessler Carriage House

Second floor carriage house in historic Indianapolis neighborhood. Renovated and with original architectural details like the hardwood floors. This cozy space is perfect for one or two people looking for a convenient midtown Indy location. Safe walkable neighborhood close to many restaurants. We've made the space a beautiful home away from home - lovely linens, fiber wifi and an excellent coffee machine. Like our space, but aren't coming to Indy? Message and we'll send you the shopping link.

Guest favorite

The bright kitchen features yellow cabinets with a white countertop and a black refrigerator. A dining area with a round wooden table and blue chairs is visible. A cozy seating arrangement, including a white sofa adorned with a yellow throw and patterned pillows, completes the inviting space.

Guesthouse in Indianapolis

4.93 out of 5 average rating, 212 reviews

Dreamy Carriage House in Historic Herron Morton

Cozy and colorful carriage house in Historic Herron Morton. Walking distance to restaurants, breakfast joints, coffee shops, downtown. Sip your coffee at the Juliette balcony, and take in the city views. Play cards till the wee hours, take an evening stroll through the neighborhood. Located on a peaceful side street in a historic Victorian neighborhood. Just north of Mass Ave and downtown. Close to I65/70, Lucas Oil Stadium, and Broadripple. Free street parking and well lit alley entrance.

Top guest favorite

A cozy living area is presented, featuring a comfortable gray sofa and an armchair with a patterned fabric. A wooden coffee table stands at center, while a light fixture and an artwork are included on the walls. Natural light filters through the white blinds of the window.

Guesthouse in Indianapolis

4.97 out of 5 average rating, 372 reviews

Hidden Orchard Guest Cottage

Enjoy your stay at our comfortable cottage, tucked away in a quiet neighborhood off the White River (10 min. from downtown & Broadripple; less than 5 min. drive from Newfields, 100 Acre Woods, and Butler University; AND walking distance to the Fitness Farm). Feel at home in this fully furnished cottage, with its up-to-date kitchen, cozy bedroom and tech-friendly living room, equipped with hi-speed Wi-Fi, Netflix and YouTube TV. There’s also a private patio with a fire pit for you to enjoy!

Top guest favorite

The cabin's exterior exhibits a rustic charm with unique angles and a mix of textures. Wooden walls are complemented by a metal roof, while multiple windows add character. A simple porch with log railings invites relaxation, surrounded by lush greenery.

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 293 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

Top guest favorite

A cozy sleeping area is highlighted by a king-sized bed adorned with a textured, light-colored quilt and a set of decorative pillows. Warm tones are complemented by vibrant curtains, while unique wall decorations add character to the space.

Guesthouse in Terre Haute

4.96 out of 5 average rating, 262 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.

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.

Top guest favorite

The living area features wooden walls and a stone fireplace, complemented by soft-glow electronic candles. A cozy armchair is positioned near a window, while a round, textured coffee table sits at the center, adorned with a vase of dried flowers.

Guesthouse in Hamilton

4.99 out of 5 average rating, 216 reviews

Waterfront Cabin | Peaceful Pondside Escape

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.

Guest favorite

A green barn structure with a metal roof is visible. The building features multiple windows and doors on the front, surrounded by well-kept grass and trees. A circular driveway approaches the barn, enhancing accessibility.

Guesthouse in Georgetown

4.92 out of 5 average rating, 225 reviews

Indian Creek Barn Cottage w/ EV & RV Charger

Private barn cottage in the knobs of Kentuckiana located on a 12 acre horse farm, recently renovated into a cozy comfortable space. The barn cottage is private space with 500 sqft, fully furnished 1 bedroom, 1 bath with living area, kitchenette equipped with a microwave, toaster, coffee maker, and mini refrigerator. Located just outside of New Albany, IN and less than 15 minutes to Louisville, KY allowing for the relaxation of the countryside, while also enjoying the city attractions!

Top guest favorite

A bright sleeping area is featured with a spacious bed adorned with a textured blanket and a decorative pillow. Two bedside tables hold lamps and small plants. A circular mirror is mounted on the wall above the bed, while the slanted ceiling adds character to the room.

Guesthouse in Bloomington

4.95 out of 5 average rating, 364 reviews

5 Min IU, Pvt Parking, Full Kitchen, Fast WiFi

🏡 Private Guesthouse ⚡️2 Miles: IU, Stadiums, DT, Golf, Lake & More⚡️ Welcome to your cozy, peaceful & thoughtfully appointed retreat! This 400 sq ft studio has a slanted ceiling; ideal for solo travelers, couples, remote workers & IU visitors. Guests love the calm vibe, spotless space & all the little extras that make it feel like home. Special Offer: Early/late check-in/check-out — $20 — Max 2-3 hours. ❤︎ Add to your wishlist by clicking the ❤︎ in the top-right corner!

Guest favorite

A cozy living area showcases wooden walls and ceiling, enhancing a rustic feel. The space features a dining table with wooden chairs, a kitchenette with a countertop, and a comfortable seating area with a television. Soft lighting adds warmth to the inviting space.

Guesthouse in Tennyson

4.9 out of 5 average rating, 115 reviews

Guest House with acreage to explore.

Relax with the whole family at this peaceful place to stay. The wooded property provides maintained walking trails for plenty of wildlife viewing pleasure and exercise. The property also features a swimming pond. Location is 8 miles from Lincoln State Park and Lincoln Amphitheater. 10 miles from Interlake State Off Road Recreation Area. 13 miles from Holiday World. 30 miles from Evansville casinos. This is a four season resort/stay, with long summers and mild winters.

Top guest favorite

A comfortable living area features a neutral-colored sofa and a wooden coffee table. A ceiling fan hangs above, while a television is mounted on the wall above a decorative fireplace. Natural light enters through two windows, complemented by rustic wall accents.

Guesthouse in Shelbyville

4.97 out of 5 average rating, 117 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.

Top guest favorite

The exterior of a wooden cabin is presented, showcasing natural logs with a rich brown hue. Flower beds filled with various plants and blooms line the base of the cabin. A white front door is framed by greenery, with steps leading up to the entrance.

Guesthouse in Rockville

4.96 out of 5 average rating, 229 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.