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
A stone-paved patio is set with a round table and six black wicker chairs, adorned with floral cushions. A vibrant red umbrella provides shade, while lush green grass and trees create a tranquil backdrop, enhancing the outdoor seating area.
Home in Walton
4.91 out of 5 average rating, 258 reviews

The Cottage at Brianza Winery

Peaceful, country setting at Brianza Gardens and Winery. Lovely ranch 2 BR/1 B has all the comforts of home incl. W/D. Enjoy the scenic views and walking trails among the gardens and vineyards. Large GR/DR, eat/n/kit. The "Cottage" is adjacent to the "Bungalow", also listed on this site. The Bungalow is a 1BR, full kitchen apartment. If you need more space please book both properties. Sorry, no pets allowed or parties. Maximum occupancy is six people. $20 fee per person/per day over four people

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Top Guest favourite
A serene outdoor area features a large swimming pond surrounded by manicured grass. Comfortable seating options include lounge chairs and umbrellas, inviting relaxation. The tranquil water reflects a clear blue sky, and a pathway leads directly to the pond, enhancing accessibility.
Cabin in Aurora
4.95 out of 5 average rating, 41 reviews

Rustic Retreat Cabin

Cozy Rustic 1800s-Inspired Cabin with Private Pond, Creek Access & 30 Acres -Located at the end of a private gravel drive, the cabin offers a peaceful retreat blending historic charm and modern comfort. Relax on the front deck with views of the pond or enjoy the back deck overlooking the creek. The loft has queen and a full bed, the basement has a full bed and futon for additional sleeping. Please note, due to the stairs and rustic decor, this cabin may not be suitable for small children.

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Superhost
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
4.87 out of 5 average rating, 102 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

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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
4.85 out of 5 average rating, 156 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.

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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, 115 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.

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Guest favourite
A cozy space features a spacious bed with a patterned quilt, complemented by a welcoming arrangement of pillows. The kitchen area is equipped with appliances and a counter with two stools. Natural light enters through the door and window, adding brightness to the room.
Tiny home in Versailles
4.94 out of 5 average rating, 16 reviews

Charming new tiny house-Friendship IN

Escape to this charming, newly built tiny house, nestled in the heart of Friendship, Indiana. This cozy retreat offers all the essentials, a fully equipped kitchen, bathroom, shower, comfortable sleeping space for two, with Wi-Fi, heat and cooling with convenient driveway parking and wheelchair accessible. Just minutes from the NMLRA grounds and walking distance to the Friendship Tavern for local favorite foods, and drinks. It is walking distance to the Hudson’s Hall and Campground.

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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, 132 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!

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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!

ValueFamilyCleanliness

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
4.97 out of 5 average rating, 545 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)

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Top Guest favourite
Dome in Vevay
4.97 out of 5 average rating, 224 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.

LocationFamilyBathroom

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, 197 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.

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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, 122 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.

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Popular amenities for Dillsboro holiday rentals

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