Vacation rentals in Dillsboro

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Top-rated vacation rentals in Dillsboro

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Top guest favorite
A historic cabin is nestled among lush greenery, showcasing a log design. A covered front porch extends from the cabin, providing a shaded area. Steps lead from the garden filled with ferns and flowers down to the riverside, where tranquility can be enjoyed.
Cabin in Union
4.91 out of 5 average rating, 149 reviews

Rustic Cabin on the Ohio River.

If you're looking for marble countertops, this may not be your place. But if you’re seeking quiet, character, and a taste of how things used to be, with a modern twist, welcome to our 1800s-era cabin. Renovated in 2022, the cabin is comfy but you can expect creaky floors, original woodwork, and a few quirks that come with age. The cabin is authentic, and thoughtfully kept. You will have TV, wifi, central heat, air conditioning but expect to hear the water pump run and there is no dishwasher.

Guest favorite
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
4.94 out of 5 average rating, 197 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.

Guest favorite
A landscaped outdoor area features blooming hydrangeas in soft pinks and whites, surrounded by gravel pathways. A fire pit area is equipped with blue chairs, and a pool is visible in the background, along with a deck overlooking the serene wooded surroundings.
Apartment in Aurora
4.88 out of 5 average rating, 112 reviews

Peaceful Paradise LOWER Fam 2BR Hot Tub/Pool/SAUNA

Located just 20 minutes from CVG airport, Perfect North Slopes, and the Creation Museum—come & enjoy a piece of Indiana in our 2 bedroom apartment! After a long day exploring our local parks or skiing on the slopes, soak in the hot tub or pool overlooking the valley or enjoy your evening by the fire pit! An in-home entertainment surround system will bring whatever movie you choose right into the room with you! Access to apartment is down stairs --not wheelchair accessible. Pool open 5/22-9/1

Superhost
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, 165 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.

Top guest favorite
A bubbling hot tub is positioned on a wooden deck, with a view of a gathering area featuring several white Adirondack chairs surrounding a fire pit. The background includes green trees and an expanse of open grass under a clear blue sky.
Cabin in Rising Sun
4.99 out of 5 average rating, 117 reviews

Cheerful 2 BR cabin on 48 acres with ponds/firepit

From the bubbling hot tub, take in the country air and tranquility at this breathtaking 48 acre (completely private) two bedroom, two bath cabin centrally located between the Ark and the Creation Museum. Enjoy a cup of coffee or glass of wine around the majestic firepit overlooking the rolling meadows. Enjoy pristine ponds (with LED fountains) to fish and swim. Watch deer and turkey roam the property. Hike the trails which include a frisbee golf course designed to take in the scenery.

Guest favorite
A single-story house is set on a grassy lawn, surrounded by lush green trees. A fire pit is visible in the foreground, with a few chairs placed nearby. A wooden clothesline stand is also present, enhancing the outdoor space's rural charm.
Home in Versailles
5 out of 5 average rating, 18 reviews

Friendship Peaceful Country Getaway

Country living less than an hour from Cincinnati. This 80 acre property features fishing, paddle boating & many walking trails. Located near beautiful Versailles State park, small town charm in Madison, Indiana & Clifty Falls State Park. The Red Wolf Sanctuary & Raptor Rehabilitation center (by appt only) is within a 40 min drive. Within 2 miles of Friendship, Indiana, home of the National Muzzleloader Rifle Association shooting competitions and famous fleamarket in June and September.

Top guest favorite
The cabin showcases a rustic exterior made of natural wood, featuring a welcoming front porch with wooden railings. Surrounding foliage displays autumn colors, enhancing the serene setting. A driveway leads to a garage door, while steps ascend to the main entry of the cabin.
Cabin in Madison
4.98 out of 5 average rating, 787 reviews

Cabin on the Ridge

Welcome to Cabin on the Ridge, your tranquil retreat nestled in the scenic hills of Madison, Indiana. Just 25 minutes from downtown Madison, our cabin offers a perfect blend of rustic charm and modern comfort. Madison, awarded the “Best Small Town in the Midwest” by USA Today and the Great American Main Street Award, is a must-visit. Enjoy the historic architecture, boutique shops, and delightful eats, or explore Clifty Falls State Park. •Fast wifi •Roku TV/Streaming services •Keurig

Top guest favorite
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, 136 reviews

The Dibble Treehouse

Welcome to The Dibble Treehouse! This cozy haven accommodates 4 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 your stay 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 favorite
Cabin in Versailles
5 out of 5 average rating, 21 reviews

Cabin on Versailles State Park Lake

Tucked along the lake at Versailles State Park, this cozy rustic cabin is perfect for individuals, couples, families and friends. It features 2 bedrooms, 2 bathrooms, a full kitchen, and a comfortable living area with lake views. Enjoy a private deck for relaxing, plus easy nearby access to hiking, fishing, and kayaking. A peaceful, secluded, nature-filled getaway with all the comforts of home and yet within walking distance of town. This is a brand new listing!

Superhost
A wooden gazebo is situated on a grassy area surrounded by trees. A picnic table is positioned nearby, offering a relaxing spot for gatherings. The landscape features patches of grass and a walking path that meanders through the outdoor space.
Home in Dillsboro
5 out of 5 average rating, 10 reviews

Wheelock Lake Campground Lodge

This beautiful and spacious three-bedroom lodge at Wheelock Lake Campground sleeps nine, featuring three queen beds and a bunk bed with trundle. With three bathrooms, it’s perfect for large groups, and boasts a large kitchen, cozy living room, and separate dining room. Outside, enjoy a gazebo and firepit for gatherings. Wheelock Lake is an ideal spot for family and friends—bring everyone along to this wonderful place with plenty of room for fun!

Top guest favorite
Dome in Vevay
4.97 out of 5 average rating, 242 reviews

Hilltop Dome, 42 secluded acres in nature

Our Geodome is tucked away on 42 private acres exclusively for you and your guest Enjoy the stars at night, fire pit, hot tub, high speed internet, washer dryer, and smart TV . The Dome is equipped with a 2 ton mini split that will keep you warm in the winter and cool in the summer We are conveniently located within 15 miles of Madison, IN, Vevay, IN, Clifty Falls, Belterra Casino, also within 62 miles of Cincinnati and Louisville.

Top guest favorite
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
4.98 out of 5 average rating, 203 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 vacation rentals