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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (31 reviews)
"The property is very well maintained, house was very cozy and relaxing. The host was great to communicate with."
United States
Tammy
The price is ￥21,372
￥34,239 total
includes taxes & fees
Oct 19 - Oct 20
Hillsboro Driftless Guesthouse is cozy and ready for you!
A wooden cabin with a porch, deck, and outdoor seating area.

2. 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, (8 reviews)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
The price is ￥19,789
￥28,727 total
includes taxes & fees
Oct 14 - Oct 15
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

3. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (15 reviews)
"Sweet home! Loved all the bright colored decorations! We had a great stay here with our bikes and pups. The porch was lovely to watch a thunderstorm from as well!"
United States
Emily B.
The price is ￥31,662
￥41,420 total
includes taxes & fees
Oct 12 - Oct 13
Colorful getaway in friendly Driftless village
A wooden deck with a barbecue grill, overlooking a river and autumn foliage.

4. 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 ￥10,290
￥19,208 total
includes taxes & fees
Oct 12 - Oct 13
Blakley Hobbit Small Cabin
A rustic wooden cabin with a front porch, a staircase, and a small deck area.

5. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (47 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 ￥14,248
￥26,723 total
includes taxes & fees
Oct 12 - Oct 13
Blakley Hobbit Large Cabin
Two white hammocks hanging on a wooden porch with a view of a garden.

6. 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, (87 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is ￥21,348
￥49,579 total
includes taxes & fees
Oct 13 - Oct 14
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
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 ￥12,918
￥46,708 total
includes taxes & fees
Nov 1 - Nov 2
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC
Two dogs sitting on a grassy field with a pond and trees in the background.

8. 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 ￥7,916
￥11,692 total
includes taxes & fees
Oct 13 - Oct 14
Blakley Hobbit Campground-RV spot #4
A cozy cabin interior with wooden walls, a stone fireplace, a dining area, and a kitchen with a large island.

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, (5 reviews)
"Beautiful cozy cabin! Loved the gas fireplace! The cabin had everything we needed and we enjoyed our stay."
United States
Monica P.
The price is ￥24,364
￥58,106 total
includes taxes & fees
Oct 12 - Oct 13
Soothing cabin 1 out of 7 in New Lisbon
A spacious kitchen with wooden cabinets, a central island with stools, a dining area with a round table and chairs, and a ceiling fan.

10. 6 Bedroom Home in Gods Country

6 Bedroom Home in Gods Country
Wilton
9.8 out of 10, Exceptional, (26 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 ￥85,487
￥112,569 total
includes taxes & fees
Oct 12 - Oct 13
6 Bedroom Home in Gods Country
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

11. 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, (18 reviews)
"excellent out of the way retreat close to things we wanted to do and great place for us and our cats, the hot tub was a great treat"
United States
Joseph W.
The price is ￥28,496
￥49,605 total
includes taxes & fees
Oct 12 - Oct 13
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
A covered deck with outdoor furniture, a small table, and a grill.

12. 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, (35 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is ￥54,000
￥112,755 total
includes taxes & fees
Oct 13 - Oct 14
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

13. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (34 reviews)
"A great place to get away and relax."
United States
Betsy D.
The price is ￥32,295
￥38,916 total
includes taxes & fees
Oct 14 - Oct 15
Your adventure begins the second you arrive!
Two dogs sitting on a grassy field with a pond and trees in the background.

14. #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 ￥3,166
￥6,680 total
includes taxes & fees
Oct 14 - Oct 15
#4 Blakley Hobbit Campground-Tent spot
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

15. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (62 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 ￥25,330
￥40,084 total
includes taxes & fees
Oct 20 - Oct 21
The Honey Haven
A wooden cabin surrounded by snow-covered trees.

16. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (53 reviews)
"This is a beautiful place to spend a couple of relaxing days. "
United States
Sujhey B.
The price is ￥24,649
￥50,278 total
includes taxes & fees
Oct 18 - Oct 19
Cabin on the Kickapoo
Two dogs sitting on a grassy field with a pond and trees in the background.

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 ￥3,166
￥6,680 total
includes taxes & fees
Oct 13 - Oct 14
#9 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

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 ￥3,166
￥6,680 total
includes taxes & fees
Oct 14 - Oct 15
#10 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

19. 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 ￥7,916
￥11,692 total
includes taxes & fees
Oct 13 - Oct 14
Blakley Hobbit Campground-RV spot #1
Two dogs sitting on a grassy field with a pond and trees in the background.

20. 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 ￥7,916
￥11,692 total
includes taxes & fees
Oct 13 - Oct 14
Blakley Hobbit Campground-RV spot #3
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

Comfort Inn & Suites New Lisbon

Comfort Inn & Suites New Lisbon

10/10 Excellent
"Incredibly clean and great price for myself as I’m driving across the continent. Thanks from Canada!"
Jakob 1-night trip
Posted 2 days ago
Comfort Inn & Suites New Lisbon

Find out more about Hillsboro

Search for holiday rentals in Hillsboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsboro using one of the methods below:

  • View our selection of featured holiday rentals in Hillsboro
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  • Enter your travel dates to view the best deals on holiday rentals in Hillsboro while they last

Look no further and take a look at our great range of rental properties in Hillsboro!

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.