Guesthouse vacation rentals in Southern Indiana

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Top-rated guesthouse rentals in Southern Indiana

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Top guest favorite
An indoor heated pool is enclosed within a greenhouse, surrounded by lush greenery and potted plants. The water appears inviting and clear, reflecting the natural light filtering through the translucent roof. Decorative elements, including sculptures, enhance the tranquil atmosphere.
Guesthouse in Dayton
4.97 out of 5 average rating, 157 reviews

Art Studio at Turtle Hill, 5-Acre Oasis Near City

The Art Studio at Turtle Hill is located in Dayton, Ky, 2.2 miles from downtown Cincinnati. The studio is situated on 5 acres overlooking the Ohio River making it a unique urban location that feels like a country setting. The main house has a heated enclosed pool that is available to guests, a fire pit and pond. The studio has a full laundry, full kitchen and 4 off-street parking spots. The main bedroom (one queen) is on the first floor and the second bedroom (2 twins) is a loft. No cleaning fee

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, 380 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
An aerial view captures a serene swimming pool surrounded by a spacious patio. A separate guest house is visible near the pool, featuring a sloped roof and multiple windows. Lush landscaping offers privacy, while a clear pathway leads from the pool area to the nearby road.
Guesthouse in Evansville
4.86 out of 5 average rating, 237 reviews

Private Guest House close to everything!

The Private Guest House is set on our property which is located on a corner (1.5 acre lot) close to the east side of Evansville. The convenient large circle drive makes it easy to enter and exit. The east side of Evansville offers Malls, Shopping, Restaurants, Bars, Entertainment, Gyms, Starbucks, and Theaters. The property is located only 10 minutes from Downtown and the Ford Center due to close proximity to Lloyd Expressway. Check out the Casino and Riverfront if you’re in the Downtown Area!

Top guest favorite
Guesthouse in Bloomington
4.96 out of 5 average rating, 394 reviews

Private Studio, 5 Min IU, Parking, Full Kitchen

Bloomington’s smallest private studio, intentionally designed to feel comfortable, calm, and easy to settle in. At ~400 sq ft with a slanted ceiling, it's ideal for solo travelers or couples who prioritize privacy, cleanliness, and thoughtful details over extra space. Guests describe the studio as cozy, spotless, and surprisingly well-equipped — with everything needed for a comfortable stay. Minutes from IU, downtown, dining, parks, and Kroger, you’re close to everything without the hassle.

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, 327 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
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, 237 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.

Top guest favorite
A charming exterior of a two-story guest suite is presented, featuring a light yellow facade with white trim. Two garage doors are visibly centered at the front, flanked by tall windows. Neatly maintained landscaping adds a touch of greenery to the entryway.
Guesthouse in Cincinnati
4.97 out of 5 average rating, 139 reviews

Bright & Cozy 1BR in Charming Mt Adams + Parking

Spacious 1 bedroom guest suite in the heart of Mt. Adams. Steps away from Holy Cross Monastery. Walk to plenty of restaurants, parks, nightlife and entertainment. Mt. Adams is surrounded by one of Cincinnati's finest parks- Eden Park, and includes landmarks such as Cincinnati Art Museum, Playhouse in the Park, and Krohn Conservatory. 10 minute walk to casino 15 minute walk to stadiums 20 minute walk to OTR 10 minute drive to hospitals Perfect for extended stay, or a weekend visit.

Top guest favorite
The charming cottage is set against a backdrop of lush greenery, featuring a welcoming front porch with two chairs. The exterior showcases light grey siding complemented by red shutters and door, while a clear driveway leads to the entrance.
Guesthouse in Cecilia
4.92 out of 5 average rating, 106 reviews

Cottage at the Hundred Acre Wood

Escape to the country and take it easy at this unique and tranquil getaway. This beautiful cottage shares the yard and scenery with the owner’s residence, but is a very peaceful & nice space to relax and sleep at the end of your day. You’ll be out in the country but still conveniently located, only about 15 min from everything. 16 minutes from Glendale - Ford Blue Oval plant 14 minutes from Etown Sports Park 16 minutes from downtown Etown & all the great restaurants and stores

Top guest favorite
A charming stone patio is surrounded by lush greenery and colorful flowers. A large umbrella provides shade over a black metal table and chairs, inviting relaxation. A decorative circular stone is positioned nearby, complementing the natural landscape.
Guesthouse in Madison
4.98 out of 5 average rating, 293 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!

Top guest favorite
A spacious bedroom features a large bed with dark bedding centered on wooden floors. Two cozy armchairs are positioned nearby, complemented by a vibrant area rug. A decorative mirror and framed artworks adorn the walls, while a bookshelf holds an array of books, adding character to the space.
Guesthouse in Louisville
4.96 out of 5 average rating, 241 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.

Guest favorite
The exterior of a two-story guest house is surrounded by autumn foliage, showcasing wooden decking with a railing. The entrance features large windows, allowing natural light to brighten the space. A pathway leads from the front, bordered by seasonal plants.
Guesthouse in Brownsburg
4.86 out of 5 average rating, 581 reviews

Cozy Guest House in the Big Woods

Guest house located in the rear grounds of main home. Sidewalk access. 20 minute drive to downtown Indy.Full kitchen & 3/4 bath. This means toilet, sink & 42" shower (no tub).Entire house can sleep 1-3. Price is for 2 guests. Add’l fees for add’l guests & pets (no pit bulls) The upstairs has a king bed & down stairs a twin futon. This area is heavily wooded so the occasional critter can be seen & there will be spiders from time to time (part of wooded living).

Top guest favorite
A cozy sitting area is furnished with two slender armchairs and a small ottoman, placed on a decorative rug. A flat-screen TV is mounted on the wall, and a narrow table holds decorative items. Sliding doors lead into the bedroom, enhancing the open feel.
Guesthouse in Louisville
4.97 out of 5 average rating, 818 reviews

Germantown Carriage House w/garage

Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. The carriage house has all the amenities for any length of stay, including garage parking with room for bikes. Only 2 miles from downtown Louisville, Germantown is nestled between the energetic and historic Highlands neighborhood, beautiful historic Old Louisville, and hipster NULU. Keyless entry makes for seamless check in and out.

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