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Dillsboro Holiday Rentals

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Our top choices for Dillsboro holiday rentals

1. King Bed|Smoking|Aurora

King Bed|Smoking|Aurora
Aurora, IN
10.0 out of 10, Exceptional, (70 reviews)
"Room offered great privacy which is important when traveling with family, would definitely come back next time we're in town!"
United States
Anonymous traveller
The price is NZ$183
includes taxes & fees
31 Aug - 1 Sept
King Bed|Smoking|Aurora

2. Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (3 reviews)
"This tiny home was exactly what we had expected. Very clean, nice and welcoming. The owners were great and communication was excellent. We will be sure to see if it is Ava when we come to visit family again. "
United States
Randall B.
The price is NZ$325
includes taxes & fees
21 Sept - 22 Sept
Charming new tiny house-Friendship IN

3. 2 Queen Beds|Non Smoking

2 Queen Beds|Non Smoking
Aurora, IN
10.0 out of 10, Exceptional, (76 reviews)
"Nice little room with all the basics covered,just what we wanted for our stay!"
United States
Anonymous traveller
The price is NZ$197
includes taxes & fees
31 Aug - 1 Sept
2 Queen Beds|Non Smoking

4. 2 Queen Bed Smoking | Hillcrest

2 Queen Bed Smoking | Hillcrest
Aurora, IN
10.0 out of 10, Exceptional, (72 reviews)
"Great spot near local attractions. Clean rooms and easy parking."
United States
Anonymous traveller
The price is NZ$197
includes taxes & fees
31 Aug - 1 Sept
2 Queen Bed Smoking | Hillcrest

5. King Bed|Non-Smoking

King Bed|Non-Smoking
Aurora, IN
10.0 out of 10, Exceptional, (74 reviews)
"Four nights of peace in Aurora! Quiet location close to local attractions like the Creation Museum was really handy for us."
United States
Anonymous traveller
The price is NZ$183
includes taxes & fees
31 Aug - 1 Sept
King Bed|Non-Smoking

6. River City Escape

River City Escape
Lawrenceburg
9.6 out of 10, Exceptional, (5 reviews)
"Really nice place, and great location! Very walkable neighborhood!"
United States
Kelly P.
The price is NZ$363
includes taxes & fees
8 Sept - 9 Sept
River City Escape

7. Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is NZ$412
includes taxes & fees
7 Sept - 8 Sept
Cabin on the Ridge: The Sequel

8. Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (7 reviews)
"A lovely accommodation! The cabin was spotless, well kept and comfortable, and the property was private and quiet. Great hosts that were very responsive and quick to help with anything. Would absolutely recommend!"
United States
Shirley Z.
The price is NZ$283
includes taxes & fees
8 Sept - 9 Sept
Briar Ridge Cabin in Osgood IN

9. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is NZ$396
includes taxes & fees
30 Aug - 31 Aug
Cabin on the Ridge

10. The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (28 reviews)
"It was great"
United States
James H.
The price is NZ$300
includes taxes & fees
1 Sept - 2 Sept
The Blue Door Place

11. Quiet Indiana Getaway w/ Game Room

Quiet Indiana Getaway w/ Game Room
Moores Hill
9.4 out of 10, Exceptional, (32 reviews)
"This property is clean, very private, and just flat out great for a relaxing time with family!"
United States
Timothy
Quiet Indiana Getaway w/ Game Room

12. Liberty Alley Hideaway 2

Liberty Alley Hideaway 2
Lawrenceburg
The price is NZ$424
includes taxes & fees
10 Sept - 11 Sept
Liberty Alley Hideaway 2

13. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is NZ$262
includes taxes & fees
7 Sept - 8 Sept
Sassafras Woodland Cabin at Lost Trails

14. The Hive.. lots of activities within walking distance-

The Hive.. lots of activities within walking distance-
Lawrenceburg
10.0 out of 10, Exceptional, (45 reviews)
"Lovely place! So nice to stay somewhere that is well decorated and accommodating!"
United States
S G.
The price is NZ$499
includes taxes & fees
31 Aug - 1 Sept
The Hive.. lots of activities within walking distance-

15. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is NZ$291
includes taxes & fees
31 Aug - 1 Sept
Maple Cozy Cabin at Lost Trails

16. Beautiful lower level of house in nature with wildlife all around.

Beautiful lower level of house in nature with wildlife all around.
UNION
10.0 out of 10, Exceptional, (21 reviews)
"We had a great stay! Our hosts were quick to reply and very helpful. We enjoyed the beautiful, private views and remote cozy location. It served our needs and then some. The beds, pillows and linens were very comfortable and clean."
United States
Melinda O.
The price is NZ$321
includes taxes & fees
31 Aug - 1 Sept
Beautiful lower level of house in nature with wildlife all around.

17. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is NZ$291
includes taxes & fees
30 Aug - 31 Aug
Walnut Secluded Cabin at Lost Trails

18. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"
United States
Emily I.
Mulberry Secluded Cabin at Lost Trails

19. Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Aurora
10.0 out of 10, Exceptional, (61 reviews)
"Happy with our stay and house "
United States
Manda C.
The price is NZ$883
includes taxes & fees
1 Sept - 2 Sept
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

20. School Days

School Days
Versailles
10.0 out of 10, Exceptional, (1 review)
"The Schoolhouse was a unique experience that we enjoyed very much! We were provided with anything that we would have needed for a comfortable stay. Our host communicated promptly whenever we needed. We appreciated the cleaniless of the home. We did not realize how close in proximity we would be with the other rentals on the property, but once inside, we felt like we had privacy. This would be a great stay for a couple or small family."
United States
Lora S.
The price is NZ$329
includes taxes & fees
20 Sept - 21 Sept
School Days
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

Find out more about Dillsboro

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Dillsboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Dillsboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Dillsboro. Seeing all the best attractions is bound to make you fall in love with Dillsboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Dillsboro short-term rentals, that won’t be hard to do.

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?

Large Family Home with Backyard Oasis & Fire Pit: This holiday home rental outside of Dillsboro offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Dillsboro?

Explore the area and family-friendly sights such as Adventure Bay, or get out into nature at a spot like Hidden Valley Lake Beach. 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.