Holiday houses in Dillsboro

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Top-rated holiday rentals in Dillsboro

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Lawrenceburg
4.96 out of 5 average rating, 126 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.

Guest favourite
A full kitchen features a large marble island with seating for four and stainless steel appliances. Exposed stone walls and wooden beams add character, while open shelving displays decorative items. Drawers and cabinets are located in the background, providing ample storage.
Home in Versailles
4.94 out of 5 average rating, 182 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 favourite
The kitchen features an arched brick wall with modern cabinetry and stainless steel appliances. Wood countertops complement the rich hardwood flooring. A polished chandelier hangs above, providing a blend of contemporary and historic elements in the space.
Apartment in Aurora
4.85 out of 5 average rating, 153 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 favourite
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, 113 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 favourite
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
4.98 out of 5 average rating, 253 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 favourite
A cozy great room features wooden walls and vaulted ceilings. A stone fireplace sits invitingly in one corner, while a comfortable sectional and two armchairs are arranged around a round coffee table. Tall windows allow natural light to fill the space, enhancing the warm ambiance.
Cabin in Madison
4.98 out of 5 average rating, 772 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 favourite
The exterior of a house is shown at sunset, featuring a welcoming porch adorned with lights. A clear pathway leads to the front door, flanked by trees. Soft glow from the house highlights the inviting atmosphere, and a decorated wreath is visible on the door.
Home in Florence
4.97 out of 5 average rating, 150 reviews

The Little Farm House

Relax with the whole family at this peaceful place to stay. King size bed in master bedroom and garden tub in master bath. There is also a full bathroom just as you enter the the back door. There are no bathrooms upstairs however, there are two bedrooms and each bedroom has a queen size bed and two twins beds built in the wall. Beautiful scenery no matter what side of the house your on. Relax on the wrap around porch and enjoy the unforgettable sunsets and different types of wildlife.

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, 129 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!

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
4.98 out of 5 average rating, 148 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
Dome in Vevay
4.97 out of 5 average rating, 219 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 favourite
Home in Dillsboro
4.97 out of 5 average rating, 194 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.

Top Guest favourite
A spacious two-story home with a distinctive red metal roof sits on a well-maintained grassy area. Surrounding trees and shrubs complement the landscape, while a gravel driveway leads to a nearby garage. A peaceful setting is showcased, with open fields visible in the background.
Home in Madison
5 out of 5 average rating, 121 reviews

Vineyard Château - peaceful country setting!

Forget your worries in this spacious and serene space. A beautiful three bedroom home, located between two historic towns of Vevay and Madison, Indiana. Perfect location for some rest & relaxation. Private country setting, just a short drive away from antiques, restaurants, state parks, and Splinter Ridge Hunting Reserve. Please note: The home is located 13 miles east of downtown Madison, approximately a 20 minute drive.

Popular amenities for Dillsboro holiday rentals

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