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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Hillsboro vacation rentals

A living room with a television, a coffee table, a sofa, and a dining area in the background.

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, (33 reviews)
"The property is very well maintained, house was very cozy and relaxing. The host was great to communicate with."
United States
Tammy
Hillsboro Driftless Guesthouse is cozy and ready for you!
A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

2. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (16 reviews)
"This is a cozy house with an excellent location, as we were biking and this is walking distance from the bike trail. We were a party of four and werenicely satisfied. We were very happy with communications!"
United States
Denise L.
Colorful getaway in friendly Driftless village
Two dogs sitting on a grassy field with a pond and trees in the background.

3. Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4
Viola
10.0 out of 10, Exceptional, (3 reviews)
"Amazing location"
United States
Paul K.
The price is AED 184
AED 240 total
includes taxes & fees
14 Nov - 15 Nov
Blakley Hobbit Campground-RV spot #4
Two white hammocks hanging on a wooden porch with a view of a garden.

4. 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, (91 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is AED 519
AED 1,121 total
includes taxes & fees
15 Nov - 16 Nov
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
A wooden deck with a barbecue grill, overlooking a river and autumn foliage.

5. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (58 reviews)
"fishing cabin."
United States
joe
The price is AED 239
AED 415 total
includes taxes & fees
19 Nov - 20 Nov
Blakley Hobbit Small Cabin
A rustic wooden cabin with a front porch, a staircase, and a small deck area.

6. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (50 reviews)
"A quiet spot w excellent scenery along the Kickapoo River. Great communication w host & easy check-in/out process."
United States
Rebecca B.
The price is AED 331
AED 589 total
includes taxes & fees
15 Nov - 16 Nov
Blakley Hobbit Large Cabin
A modern living room with a sectional sofa, a wooden coffee table, and a dining area with a white table and chairs.

7. 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
8.0 out of 10, Very good, (2 reviews)
"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 AED 313
AED 1,001 total
includes taxes & fees
30 Nov - 1 Dec
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC
A cozy cabin interior with wooden walls, a stone fireplace, a dining area, and a kitchen with a large island.

8. Soothing cabin 1 out of 7 in New Lisbon

Soothing cabin 1 out of 7 in New Lisbon
New Lisbon
9.4 out of 10, Exceptional, (8 reviews)
"Great location. Met our needs perfectly"
United States
Tricia C.
The price is AED 565
AED 1,278 total
includes taxes & fees
14 Nov - 15 Nov
Soothing cabin 1 out of 7 in New Lisbon
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

9. 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
9.2 out of 10, Wonderful, (22 reviews)
"Property fit our needs perfectly and check in and check out was easy!"
United States
Scott C.
The price is AED 661
AED 1,097 total
includes taxes & fees
14 Nov - 15 Nov
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

10. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (35 reviews)
"A great place to get away and relax."
United States
Betsy D.
The price is AED 617
AED 709 total
includes taxes & fees
18 Nov - 19 Nov
Your adventure begins the second you arrive!
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

11. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (64 reviews)
"This was my second time staying at the Honey Haven and I would love to stay again. The host does a wonderful job keeping the property in great shape and the area that the property is in is so special."
United States
Eric R.
The price is AED 617
AED 876 total
includes taxes & fees
16 Nov - 17 Nov
The Honey Haven
A wooden cabin surrounded by snow-covered trees.

12. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (55 reviews)
"This is a beautiful place to spend a couple of relaxing days. "
United States
Sujhey B.
The price is AED 502
AED 1,027 total
includes taxes & fees
17 Nov - 18 Nov
Cabin on the Kickapoo
A spacious kitchen with wooden cabinets, a central island with stools, a dining area with a round table and chairs, and a ceiling fan.

13. 6 Bedroom Home in Gods Country

6 Bedroom Home in Gods Country
Wilton
9.8 out of 10, Exceptional, (27 reviews)
"It’s the good house and all the bed rooms have attached bathroom. Suggest to the homeowner is that keeping the bath shower and moisturizer at each room"
United States
Rambabu
The price is AED 1,983
AED 2,484 total
includes taxes & fees
14 Nov - 15 Nov
6 Bedroom Home in Gods Country
A covered deck with outdoor furniture, a small table, and a grill.

14. Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Norwalk
9.6 out of 10, Exceptional, (36 reviews)
"Great location for our family outing. Plenty of room for everyone and a nice deck for relaxing outside. Easy ride to the Kickapoo River as well as surrounding towns for a little bumming."
United States
Dawn C.
The price is AED 1,833
AED 3,150 total
includes taxes & fees
24 Nov - 25 Nov
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Two dogs sitting on a grassy field with a pond and trees in the background.

15. #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 AED 73
AED 124 total
includes taxes & fees
14 Nov - 15 Nov
#4 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

16. Blakley Hobbit Campground-RV spot #1

Blakley Hobbit Campground-RV spot #1
Viola
9.0 out of 10, Wonderful, (4 reviews)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
The price is AED 184
AED 240 total
includes taxes & fees
14 Nov - 15 Nov
Blakley Hobbit Campground-RV spot #1
Two dogs sitting on a grassy field with a pond and trees in the background.

17. #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 AED 73
AED 124 total
includes taxes & fees
14 Nov - 15 Nov
#10 Blakley Hobbit Campground-Tent spot
A modern interior with a wooden ceiling, a grey sofa, a staircase, and a kitchen area.

18. The Incline

The Incline
Norwalk
10.0 out of 10, Exceptional, (7 reviews)
"This place is a perfect couples getaway! "
United States
Kurt T.
The Incline
Two dogs sitting on a grassy field with a pond and trees in the background.

19. Blakley Hobbit Campground-RV spot #3

Blakley Hobbit Campground-RV spot #3
Viola
6.0 out of 10, (1 review)
"This is a beautiful property. The price is a little high for the lack of amenities and the road was busier than I expected but we loved the place anyhow. "
United States
Kirstin
The price is AED 184
AED 240 total
includes taxes & fees
14 Nov - 15 Nov
Blakley Hobbit Campground-RV spot #3
Two dogs sitting on a grassy field with a pond and trees in the background.

20. #8 Blakley Hobbit Campground-Tent spot

#8 Blakley Hobbit Campground-Tent spot
Viola
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed the campground very much. A little lacking in facilities but location makes up for it in spades!"
United States
Nicholas B.
The price is AED 73
AED 124 total
includes taxes & fees
14 Nov - 15 Nov
#8 Blakley Hobbit Campground-Tent spot
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

Super 8 by Wyndham Reedsburg

Super 8 by Wyndham Reedsburg

10/10 Excellent
"Nothing bad to say decent rates and clean amenities"
Clint 4-night trip
Posted 19 hours ago
Super 8 by Wyndham Reedsburg

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?

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes: This vacation home near Hillsboro is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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.