Holiday houses in Dillsboro

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Top-rated holiday rentals in Dillsboro

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Guest favourite
The exterior of a charming single-story home is displayed, featuring a covered front porch with seating. Lush greenery and flowers are visible in the landscaping. A paved driveway leads to a garage, with additional parking available on the street. A clear blue sky adds to the inviting scene.
Home in Lawrenceburg
4.98 out of 5 average rating, 111 reviews

The Hive

This comfy & cozy home is located in the heart of downtown Lawrenceburg and is within walking distance to everything! We have a large back yard that is great for family to hang out by fire-pit and enjoy their time away from home. There is large outdoor tv with adirondack chairs and picnic tables for relaxing. Living Room has 75' Tv- both bedrooms have 55' tv's. Large Sectional in Living room and large dining table in kitchen. Coffee bar- Washer & Dryer-Front Porch- Fenced in back yard.

Top Guest favourite
The modern treehouse is showcased with a yellow deck extending from the entrance, situated on a gravel driveway. Large windows invite natural light, while the surrounding trees add to the natural setting. The structure appears elevated, resting on concrete stilts.
Treehouse in Rising Sun
4.98 out of 5 average rating, 105 reviews

The Dibble Treehouse

Welcome to The Dibble Treehouse! This cozy haven accommodates 4-6 guests and boasts all the amenities for an unforgettable stay. Relax in the hot tub or sauna, gently swing in the suspended bed or hanging chairs, and savor meals at the outdoor picnic table. The full kitchen is equipped for culinary adventures and the wrap around porch offers stunning views. Enjoy evenings by the fire pit or take in your favorite shows on the smart TV. Book this stay to fully recharge and reconnect with nature!

Top Guest favourite
The exterior of a historic two-story building is presented, featuring a white facade with distinctive architectural details. Warm lighting illuminates the entrance and surrounding area, while a tree with sparse branches is visible in the foreground. The setting reflects a calm evening atmosphere.
Apartment in Lawrenceburg
4.97 out of 5 average rating, 143 reviews

The Dunn Houses on Elm Row

Welcome to the Dunn Houses on Elm Row, we are 15 mins, from CVG Airport and the Cincinnati/N.Kentucky area. We have the quaintness of a small town, but the ability to keep you busy. You can try your hand at slots, enjoy a concert, dine at one of many restaurants/bar, or enjoy nature with the bike/walking trail or the many parks locally. At the Dunn Houses, we will go out of our way to make your stay memorable. We hope when you stay with us, you experience what makes Lawrenceburg so special.

Top Guest favourite
An exterior view of the reconstructed stone schoolhouse is shown, featuring a peaked roof and a large entry door. Two potted plants flank the entrance. A leafy tree provides shade on a grassy area, with open fields visible in the background under a clear blue sky.
Home in Versailles
4.95 out of 5 average rating, 148 reviews

School Days

Sharpen your pencils and reminisce about your childhood school days in this beautifully reconstructed schoolhouse. Built in 1879, this gorgeous property is situated just minutes from local coffee shops, locally owned restaurants, antique shops and the second largest State Park in Indiana. Be entertained with live music, museums, and other attractions by visiting three conveniently located cities. Come enjoy the modern amenities as well as the historical features this schoolhouse has to offer.

Top Guest favourite
The cozy sleeping area features light wood paneling and a spacious bed adorned with blue and floral bedding. A striking black and white artwork hangs on the wall, complemented by a vintage-inspired hanging light fixture. Natural light enters through the window, enhancing the serene environment.
Tiny home in Florence
4.85 out of 5 average rating, 116 reviews

New Tiny House, Ohio River view, running water,

This small, 1 room, new tiny house called “The Lite House” is decorated shabby chic and located in a beautiful wooded setting facing a cove at a marina with views of the water on the Ohio River. Catch beautiful sunrises here. There are shared places on the property guests can use while staying, a covered shelter with grills, supplies, tables, chairs, fire pit, side walks. You will use the restrooms in the shelter, just 5 steps away from your door. Umbrella provided in tiny house. See photos.

Guest favourite
A spacious bedroom features a comfortable bed with white linens, complemented by a tufted bench at the foot. Exposed brick walls contrast with sleek modern appliances in the kitchen area, while warm wood flooring and soft lighting create a cozy ambiance.
Apartment in Aurora
4.84 out of 5 average rating, 125 reviews

Studio Apartment w/ Beautiful View!

Come and stay a while in this charming and unique studio apartment. Located in the heart of historical Aurora, IN, you can walk to all the shops, parks and restaurants! Step out onto your private patio and enjoy your view of the Ohio River! It’s the perfect romantic getaway. We are also pet friendly so if you want to bring your furry friends we are happy to host them as well, just be aware that there is a $100 fee that covers our additional cost. Just add them with your guests at checkout.

Guest favourite
A large outdoor dining table set for six is positioned on a spacious deck, showcasing a view of the Ohio River. The table is adorned with a floral centerpiece, and the surrounding area is bordered by trees, providing a serene backdrop.
Home in Aurora
4.94 out of 5 average rating, 119 reviews

River View:Hot Tub/Creation Museum/Ark/3 King Beds

🏡 Spacious 4BR/3.5BA riverview retreat with 2 king master suites — sleeps 11! 🛏️ 3 King Bedrooms + a fun bunkroom for kids. 🌅 Enjoy river view sunrises. 💦 Relax in the private hot tub. 🍳 Fully stocked kitchen for easy meals. 🎲 Family-friendly with games & puzzles. ☕️ Coffee bar. 🚲 Bikes Provided, enjoy riverside bike & walking trails. 🌳 Large outdoor area for relaxing or gathering. 🎢 Minutes to Perfect North & Creation Museum & Ark! 💫 Thoughtful touches for a comfortable stay.

Guest favourite
A single-story house displays a welcoming exterior with beige siding and red shutters. A manicured lawn is complemented by colorful flowers and shrubs in front. A solid pathway leads to the entrance, with a mailbox positioned at the edge of the property.
Home in Osgood
4.93 out of 5 average rating, 120 reviews

Wilmer Crash Pad: Simple home, includes breakfast

It's a simple 2 bed, 1 bath house that is perfect for short or long stays, depending on your needs. It is on a quiet, dead-end street with a relaxing vibe. The home is well-equipped with *everything* you would need for daily life. Family friendly with toys, games, etc. Blow-up mattress and futon for extra sleepers. Keyless entry. Two car detached garage. Perfect for work trips or area visits. One hour from Cincy, 75 minutes to Indy, 90 minutes to Louisville, 20 minutes to Batesville.

Top Guest favourite
A welcoming living area is centered around a wooden coffee table adorned with decorative items. Two comfortable sofas, equipped with cushions, invite relaxation. Natural light filters through windows, and a rustic ladder leans against the wall. A glimpse of the kitchen area can be seen in the background.
Cottage in Sunman
4.99 out of 5 average rating, 134 reviews

Phil’s Place, a comfy country cottage with hot-tub

You have found your secluded getaway from it all! Enjoy all the comforts of home in a quaint country setting. Extra amenities include a hot tub and a bottle of local wine to enjoy! Centrally located, visitors can easily explore all the Tri-state area has to offer, like Perfect North Slopes, Creation museum, antique markets, casinos, and festivals like Friendship muzzleloader shoot, Freudenfest, and Happy Valley Bluegrass. There are 3 wineries and 2 breweries all within 30 minutes!

Top Guest favourite
The cabin exterior is softly illuminated by string lights, creating a warm ambiance. Wood siding complements the design, while tall windows enhance the visual appeal. A small patio area with chairs invites relaxation in the tranquil wooded setting.
Cabin in Madison
4.98 out of 5 average rating, 502 reviews

Cabin on the Ridge: The Sequel

Welcome to the area's first new construction short term rental tailored for you, the guest. This contemporary cabin is nestled in the woods right in the heart of Amish country. This is the perfect destination for those who want to getaway yet enjoy the unique beauty of Historic Downtown Madison (25 minutes) recognized as "The prettiest small town in the Midwest" or chase waterfalls at Clifty Falls State Park (25 minutes). •Fast wifi •Roku TV •Keurig (K-Cups Available)

Top Guest favourite
An inviting living area features a plush gray sofa adorned with decorative pillows. A wooden coffee table occupies the center, and a contemporary lamp stands beside a cozy chair. Light filters through the sliding glass doors, reflecting off the warm wooden floors.
Cabin in Versailles
4.98 out of 5 average rating, 149 reviews

Mamaws Cabin Hot tub, Creation Museum/ARK, Hiking

Spacious cabin (1100 sq feet) was once Mamaw's home. Sleeps 2 private and 4 more semi-private, 6 people total. Built in a primitive country style, it features a Loft bedroom that sleeps 3, an additional small bedroom that sleeps 1 and a Master Bedroom with Queen- size Sleep Number Bed. Fully functional kitchen and bath including washer/dryer. Outdoor fire-pit and hot tub. ROKU TV/ DVDs, No cable. Wii gaming system. WiFi available.

Top Guest favourite
The exterior of a two-story brick Victorian house showcases a welcoming entrance with steps leading to a covered porch. Large windows allow ample natural light, and a well-maintained front yard complements the classic architectural features.
Home in Dillsboro
4.97 out of 5 average rating, 182 reviews

Spacious home in a quaint small town setting

This is a 1888 Victorian style two story brick house set in a neighborhood of older homes. Newly renovated with a fully equipped kitchen, laundry facility, dining room, living room, bedroom and 1 1/2 bathrooms on first floor. The second floor has three bedrooms and 2 full bathrooms. Each upstairs bedroom has a Smart TV and the living room has a Smart TV. It has a pleasant back yard with outdoor sitting and onsite parking.

Popular amenities for Dillsboro holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Dearborn County
  5. Dillsboro