
Guesthouse holiday rentals in Southern Indiana
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Top-rated Guesthouses in Southern Indiana
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

5 Min IU | Private Studio, Full Kitchen, Parking
A calm, thoughtfully designed studio created for comfort and ease. At ~400 sq ft with a charming slanted ceiling, the space is ideal for solo travelers or couples looking for a cozy stay. Guests describe the studio as spotless, cozy, and well-equipped, with everything needed to settle in. Located just minutes from IU, downtown, dining, parks, and Kroger, you’re close to it all! Note: The studio is above a detached garage. The garage door is not used during guest stays, so it will not be heard.
4.96 out of 5 average rating, 462 reviews
Lofty Lodge on the Bourbon Trail
Come to the Bourbon Trail in the Heart of Kentucky! Stay at our beautiful lodge with large common areas perfect for hanging out! Our space is great for family trips, work retreats, or a couples get away! The lodge is located just 3 miles from from restaurants, groceries, pharmacies and shops. But at the Lodge you will enjoy the peace of the country. We are central to all the bourbon distilleries: 15mi to Maker's mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington and Louisville.
4.99 out of 5 average rating, 139 reviews
Treehouse Retreat With a View of National Forest
IU Fans! 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.
4.97 out of 5 average rating, 247 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.
4.96 out of 5 average rating, 385 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, use our stand-up paddleboards, or simply enjoy sitting on the porch listening to the birds. Chances are, you may spot wild turkey or whitetail deer scampering by.
4.99 out of 5 average rating, 268 reviews
Lavish church suite with choir loft
Indulge yourself with soaring ceilings, chef's kitchen, luxurious king bed, and soaking tub, all in a landmark church surrounded by Louisville's hottest neighborhood, NULU. Our grandest renovation at the Holy Goat, The Revival Loft, lets you gaze through large, historic church windows while sipping your morning coffee or evening bourbon. Built in 1843 this former church is now home to one of Louisville's most unique guest houses, steps from the city's best food, drink, and culture.
4.99 out of 5 average rating, 107 reviews
Little Cabin in the Woods - Bent not Broken
Discover your next FAVORITE place to visit. Welcome to Always Ranch LLC where this unique, tiny cabin offers you a tranquil spot to relax and unwind. You will be surrounded by nature as we live on a horse ranch. The cabin may look crooked, but the inside it is rustic and warming. See our Guide Book for close by suggestions. We aren't too far away from local attractions. The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill.
4.97 out of 5 average rating, 378 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.
4.88 out of 5 average rating, 170 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.
4.96 out of 5 average rating, 246 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 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.
4.97 out of 5 average rating, 148 reviews
Summer Kitchen at The Hill
Come enjoy this spacious studio that has been remodeled from an old summer kitchen. Located on 6 acres in the town of Spencer, this is the perfect place to unwind and getaway, or use it as a jumping point to adventure at nearby McCormick's Creek or Cataract Falls. Walking distance to neighborhood grocery store, coffee shop, and restaurants. Within 30 minutes of Bloomington and Indiana University! The hosts live full time in the main house with 2 great danes.
4.94 out of 5 average rating, 109 reviews
HIghlands Modern Get Away
Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.
4.92 out of 5 average rating, 1255 reviewsPopular amenities for Southern Indiana guesthouses
Family-Friendly guesthouses

Hideaway Hollow
4.96 out of 5 average rating, 257 reviews
Prospect Guest House
5.0 out of 5 average rating, 137 reviews
Cottage at the Hundred Acre Wood
4.92 out of 5 average rating, 129 reviews
Private Guest House close to everything!
4.88 out of 5 average rating, 267 reviews
Garden Studio Guesthouse
4.97 out of 5 average rating, 369 reviews
Adorable Studio Apt in the Treetops of Beechmont
4.87 out of 5 average rating, 179 reviews
Highlands Carriage House
4.98 out of 5 average rating, 337 reviews
Highlands - Elegant Calm Clean & Green - Walkable
4.99 out of 5 average rating, 439 reviewsGuesthouses with a patio

*BRAND NEW* Gem of Germantown Private Derby Suite
5.0 out of 5 average rating, 347 reviews
Professional Serenity Suites
4.96 out of 5 average rating, 106 reviews
Chic Derby stay minutes from Churchill Downs!
4.9 out of 5 average rating, 115 reviews
Downtown 1 bed & 1 bath studio guest house
4.9 out of 5 average rating, 121 reviews
Charming Carriage House in Old Louisville
4.98 out of 5 average rating, 191 reviews
Studio apartment above Garage in downtown Madison
4.97 out of 5 average rating, 119 reviews
The Main St Carriage House - a charming cottage
4.94 out of 5 average rating, 131 reviews
The Goataway
4.91 out of 5 average rating, 125 reviewsGuest house rentals with a washing machine and dryer

Germantown Carriage House w/garage
4.97 out of 5 average rating, 876 reviews
The Fountain Square Flat - *No Cleaning Fee*
4.97 out of 5 average rating, 226 reviews
Perfect Downtown Carriage House - Walkable!
4.98 out of 5 average rating, 131 reviews
Twisted Creek Farm -Guest Retreat
4.92 out of 5 average rating, 407 reviews
The Cottage Next Door
4.86 out of 5 average rating, 237 reviews
Dreamy Carriage House in Historic Herron Morton
4.93 out of 5 average rating, 271 reviews
Eco-Friendly Downtown Indy Carriage House
4.96 out of 5 average rating, 369 reviews
Wishing Well Guesthouse On The Lake
4.99 out of 5 average rating, 229 reviewsDestinations to explore
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