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Top Holiday Rentals in Dillsboro

Our top choices for Dillsboro holiday rentals

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (194)
"This cabin is the perfect place to getaway and relax! It’s peaceful and beautiful!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (91)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (42)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!

Charming 2-bedroom house in Devil's Elbow Osgood, IN

10.0 out of 10, Exceptional, (2)
"House is as pictured and stated. Beds were comfortable, well stocked kitchen, nice keurig selection of coffee, beautiful outdoor setting behind house backs up to woods,very peaceful. Great place would stay again."
Charming 2-bedroom house in Devil's Elbow Osgood, IN

The Hive.. lots of activities within walking distance-

9.8 out of 10, Exceptional, (24)
"We loved our stay in Lawrenceburg. Cute town with lots of things to do nearby. The home was clean, spacious and very nice. We would definitely stay here again when we are back in Indiana. "
The price is £224
includes taxes & fees
24 Aug - 25 Aug
The Hive.. lots of activities within walking distance-

Relaxing family friendly cabin that lets you escape and enjoy nature

10.0 out of 10, Exceptional, (8)
"BEAUTIFUL property! Would definitely stay again. It was incredibly family friendly and such a perfect place for a little girls trip. The check in and check out process was super easy. Definitely will recommend to others!"
The price is £336
includes taxes & fees
28 Aug - 29 Aug
Relaxing family friendly cabin that lets you escape and enjoy nature

Grace Woods - Private Lake | Dock | Outdoor Space

10.0 out of 10, Exceptional, (1)
"Everything was excellent!"
Grace Woods - Private Lake | Dock | Outdoor Space

Never Too Far Spacious house on dead end road with great outdoor space!

10.0 out of 10, Exceptional, (27)
"The house stay was great and very comfortable and clean, which we appreciated very much!Wld definitely recommend staying here."
The price is £227
includes taxes & fees
1 Sept - 2 Sept
Never Too Far Spacious house on dead end road with great outdoor space!

Madison's Only YURT Experience

9.4 out of 10, Exceptional, (9)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
Madison's Only YURT Experience

Unique Secluded Cabin with Loft on Classified Forest

9.6 out of 10, Exceptional, (41)
"Beautiful, secluded cabin!! Loved seeing the deer each evening. If we are in this area again, we would definitely stay here!"
Unique Secluded Cabin with Loft on Classified Forest

Pet friendly cottage located between the Ark & Creation Museum

9.8 out of 10, Exceptional, (38)
"It was a birthday trip to the Arc and Museum and the house is settled almost between the two venues. The house is adorable, very clean and having two bathrooms is a big bonus. The neighborhood is quiet and a large grocery chain is just minutes away."
Pet friendly cottage located between the Ark & Creation Museum

Family Ark Adventure

9.8 out of 10, Exceptional, (26)
"We came to visit family for Christmas…also went to the Ark and the zoo. Great accommodations, quiet, comfortable, close to everything! We’ll definitely be back!"
Family Ark Adventure

Cabin on the Ridge: The Sequel

10.0 out of 10, Exceptional, (15)
"So beautiful and relaxing, very comfortable stay!"
The price is £162
includes taxes & fees
24 Aug - 25 Aug
Cabin on the Ridge: The Sequel

Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!

10.0 out of 10, Exceptional, (7)
"This was such a nice place, very quiet and peaceful. The property was everything we had hoped for and the host was so nice and helpful."
The price is £174
includes taxes & fees
25 Aug - 26 Aug
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!

KY log home close to The Ark Encounter on private 14 acres private seasonal pool

9.2 out of 10, Wonderful, (29)
"We enjoyed the space the cabin had to offer and had a great time."
KY log home close to The Ark Encounter on private 14 acres private seasonal pool

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (36)
"My small group wanted to relax in a quiet setting and Carol’s cabin was perfect. Extremely clean, well-provisioned, quiet and private with a beautiful property to stroll around. Would definitely come back!"
Carol’s Cabin in the Woods in Historic Hoosier Hills

Rivertown Ranch near Creation Museum, Ark Encounter and Perfect North Slopes

9.8 out of 10, Exceptional, (80)
"Spent a week at the home school conference with my daughters family visiting the Arc and Creation museum "
Rivertown Ranch near Creation Museum, Ark Encounter and Perfect North Slopes

The Ark's Birds Nest

10.0 out of 10, Exceptional, (4)
"Our stay at this property was absolutely wonderful! From the moment we arrived, we were impressed by how spacious and beautifully maintained the home was — it offered more than enough room for everyone to relax comfortably."
The Ark's Birds Nest

Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

10.0 out of 10, Exceptional, (306)
"My family and I truly enjoyed our stay. We love coming here it has all the amenities that added to our comfort. Hosts were very accommodating which was really appreciated. "
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

Spacious and private home. Located 2 miles from the Creation Museum. Sleeps 14.

10.0 out of 10, Exceptional, (74)
"We really enjoyed our stay."
Spacious and private home. Located 2 miles from the Creation Museum. Sleeps 14.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dillsboro Hotel Reviews

Frequently asked questions

Are there holiday rentals in Dillsboro?

Yes, there are holiday rentals close to the most popular sights in Dillsboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Dillsboro has to offer?

Charming 2-bedroom house in Devil's Elbow Osgood, IN: This holiday home rental outside of Dillsboro is located in a rural location, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Dillsboro?

Explore the area and family-friendly sights such as Competition Racing Indoor Karting Center, or get out into nature at a spot like Big Bone Lick State Historic Site. Versailles State Park and Rising Star Casino are a couple of places you'll find in the wider area.

What’s a holiday rental in Dillsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Dillsboro. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.