A forested river with clear water reflecting trees and rocky cliffs.

Hillsboro Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Hillsboro vacation rentals

Smart TV, DVD player

1. Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro Driftless Guesthouse is cozy and ready for you!
Hillsboro
10.0 out of 10, Exceptional, (29 reviews)
"The home was extremely clean, decorated nicely, very homey, had everything we needed and more! We can’t wait to return!"
United States
Brett B.
The price is SAR 483
SAR 811 total
includes taxes & fees
18 Aug - 19 Aug
Hillsboro Driftless Guesthouse is cozy and ready for you!
Exterior

2. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (14 reviews)
"It’s a cozy place with all cooking utensils you will ever need! Very comfy beds as well. "
United States
Randy R.
The price is SAR 751
SAR 998 total
includes taxes & fees
17 Aug - 18 Aug
Colorful getaway in friendly Driftless village
Exterior

3. Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Ontario
10.0 out of 10, Exceptional, (5 reviews)
"The cabin was the perfect weekend getaway for me and my husband. We were in the area to kayak the Kickapoo River and the cabin was close to where we launched (about 8 mins). It was cozy to relax in after 12.5 miles of kayaking. We enjoyed sitting outside, seeing wildlife including a deer, and hearing an owl at night. We plan to be back!"
United States
Rebecca
The price is SAR 503
SAR 721 total
includes taxes & fees
8 Sep - 9 Sep
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Exterior

4. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very Good, (45 reviews)
"Very peaceful, charming rustic cabin. I highly recommend and we plan to come back. "
United States
Jonathan C.
The price is SAR 338
SAR 634 total
includes taxes & fees
16 Aug - 17 Aug
Blakley Hobbit Large Cabin
Smart TV

5. 2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC

2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC
Reedsburg
10.0 out of 10, Exceptional, (1 review)
"I was in Reedsburg for work and this property was perfect. Had all the amenities that I needed and that were listed in the property details. I would definitely stay here again."
United States
Kerri M.
The price is SAR 306
SAR 1,108 total
includes taxes & fees
17 Aug - 18 Aug
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC
Property grounds

6. #4 Blakley Hobbit Campground-Tent spot

#4 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (2 reviews)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
The price is SAR 75
SAR 158 total
includes taxes & fees
14 Aug - 15 Aug
#4 Blakley Hobbit Campground-Tent spot
Terrace/patio

7. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (56 reviews)
"fishing cabin."
United States
joe
The price is SAR 244
SAR 456 total
includes taxes & fees
18 Aug - 19 Aug
Blakley Hobbit Small Cabin
Terrace/patio

8. Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Lyndon Station
10.0 out of 10, Exceptional, (79 reviews)
"Great location just outside of the Dells… very quiet"
United States
Gary B.
The price is SAR 518
SAR 1,192 total
includes taxes & fees
10 Sep - 11 Sep
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Interior

9. Soothing cabin 1 out of 7 in New Lisbon

Soothing cabin 1 out of 7 in New Lisbon
New Lisbon
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Met our needs perfectly"
United States
Tricia C.
The price is SAR 578
SAR 1,378 total
includes taxes & fees
25 Aug - 26 Aug
Soothing cabin 1 out of 7 in New Lisbon
Exterior

10. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (48 reviews)
"Fun little place. Perfect for me and the wife. Close to Kickapoo area hiking. Hot tub was a nice touch to the neat little stay."
United States
Joel M.
The price is SAR 551
SAR 1,152 total
includes taxes & fees
20 Aug - 21 Aug
Cabin on the Kickapoo
Interior

11. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (33 reviews)
"Enjoyed our weekend away. Definitely coming back and trying the other cabins. "
United States
Samantha N.
The price is SAR 713
SAR 860 total
includes taxes & fees
19 Aug - 20 Aug
Your adventure begins the second you arrive!
TV

12. Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells

Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells
Reedsburg
9.8 out of 10, Exceptional, (12 reviews)
"The home was very comfortable and clean. It had everything we needed and we would definitely stay here again! "
United States
Ken M.
The price is SAR 845
SAR 1,925 total
includes taxes & fees
16 Aug - 17 Aug
Perfectly located 3 bedroom house between Reedsburg and Wisconsin Dells
Smart TV, fireplace

13. Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Viola
9.0 out of 10, Wonderful, (15 reviews)
"Property was perfect for our dog. The house had everything youd need for your stay and the host was great! "
United States
Nicole Z.
The price is SAR 676
SAR 1,172 total
includes taxes & fees
18 Aug - 19 Aug
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Interior

14. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (56 reviews)
"Great place. Perfect location for the Driftless. The host were terrific."
United States
John I.
The price is SAR 601
SAR 951 total
includes taxes & fees
20 Aug - 21 Aug
The Honey Haven
Coffee/tea maker, fridge, microwave, oven

15. KwikStay: The Small-Town Ranch Style Home

KwikStay: The Small-Town Ranch Style Home
Loganville
10.0 out of 10, Exceptional, (6 reviews)
"Home was absolutely beautiful with plenty of room for everyone. Centrally located to all attractions, with short travel times. Host was amazing to work with. "
United States
Dawn B.
The price is SAR 781
SAR 942 total
includes taxes & fees
25 Aug - 26 Aug
KwikStay: The Small-Town Ranch Style Home
Property grounds

16. Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4
Viola
10.0 out of 10, Exceptional, (1 review)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
The price is SAR 188
SAR 277 total
includes taxes & fees
22 Aug - 23 Aug
Blakley Hobbit Campground-RV spot #4
Property grounds

17. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
The price is SAR 75
SAR 158 total
includes taxes & fees
14 Aug - 15 Aug
#9 Blakley Hobbit Campground-Tent spot
Property grounds

18. #10 Blakley Hobbit Campground-Tent spot

#10 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Huan B.
The price is SAR 75
SAR 158 total
includes taxes & fees
14 Aug - 15 Aug
#10 Blakley Hobbit Campground-Tent spot
Microwave, oven, stovetop, dishwasher

19. Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub

Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub
Loganville
The price is SAR 629
SAR 758 total
includes taxes & fees
25 Aug - 26 Aug
Cozy 2-bedroom apartment with Your Own Private Patio & Hot-Tub
Exterior detail

20. Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua
Viroqua
9.8 out of 10, Exceptional, (59 reviews)
"Nice place to stay right in town perfect for a couple "
United States
Pete G.
The price is SAR 357
SAR 670 total
includes taxes & fees
19 Aug - 20 Aug
Cozy first floor at the heart of downtown Viroqua
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 Hillsboro Hotel Reviews

The Lodge at Mauston

The Lodge at Mauston

10/10 Excellent
"Property was very clean. Staff was very helpful. I would recommend."
Edgar 3-night trip
Posted 2 days ago
The Lodge at Mauston

Frequently asked questions

Can I find vacation rentals in Hillsboro?

Yes, we have vacation rentals close to well known points of interest in Hillsboro, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Hillsboro has to offer?

Upper Place Vacation Cottage: This vacation home rental near Hillsboro is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

What can I see and do in Hillsboro?

While exploring the area, visit family-friendly sights like The Red Geranium Framing and Gifts, or get outside and enjoy nature at Lake Redstone. In the larger area, you’ll find Wildcat Mountain State Park and Kickapoo Valley Reserve.

What’s a vacation rental in Hillsboro like?

Vacation rentals are privately owned properties where you can stay for a couple of days or more in Hillsboro. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.