Hillsboro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (32 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 CA $191
CA $297 total
includes taxes & fees
Nov 9 - Nov 10
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.
The price is CA $280
CA $337 total
includes taxes & fees
Nov 22 - Nov 23
Colorful getaway in friendly Driftless village
A riverside park with a wooden bench, trees, and a grassy area.

3. 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 CA $127
CA $227 total
includes taxes & fees
Nov 8 - Nov 9
Blakley Hobbit Large Cabin
Two dogs sitting on a grassy field with a pond and trees in the background.

4. 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 CA $71
CA $92 total
includes taxes & fees
Nov 8 - Nov 9
Blakley Hobbit Campground-RV spot #4
A rustic cabin with a wooden deck, a small wooden structure, and a fire pit area surrounded by rocks and fallen leaves.

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 CA $92
CA $159 total
includes taxes & fees
Nov 19 - Nov 20
Blakley Hobbit Small Cabin
A modern living room with a sectional sofa, a wooden coffee table, and a dining area with a white table and chairs.

6. 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 CA $120
CA $399 total
includes taxes & fees
Dec 8 - Dec 9
2-bedroom Home in Reedsburg - 20min from Wisconsin Dells - Across from RAMC
A spacious kitchen with wooden cabinets, a central island with stools, a dining area with a round table and chairs, and a ceiling fan.

7. 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 CA $763
CA $911 total
includes taxes & fees
Nov 8 - Nov 9
6 Bedroom Home in Gods Country
Two white hammocks hanging on a wooden porch with a view of a garden.

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, (90 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is CA $215
CA $428 total
includes taxes & fees
Nov 15 - Nov 16
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
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
9.2 out of 10, Wonderful, (7 reviews)
"Great location. Met our needs perfectly"
United States
Tricia C.
The price is CA $217
CA $492 total
includes taxes & fees
Nov 8 - Nov 9
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.

10. 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, (21 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 CA $252
CA $417 total
includes taxes & fees
Dec 7 - Dec 8
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Two dogs sitting on a grassy field with a pond and trees in the background.

11. #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 CA $28
CA $47 total
includes taxes & fees
Dec 7 - Dec 8
#4 Blakley Hobbit Campground-Tent spot
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

12. 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 CA $237
CA $273 total
includes taxes & fees
Nov 18 - Nov 19
Your adventure begins the second you arrive!
Two dogs sitting on a grassy field with a pond and trees in the background.

13. #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 CA $28
CA $31 total
includes taxes & fees
Nov 9 - Nov 10
#10 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

14. 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 CA $70
CA $92 total
includes taxes & fees
Dec 7 - Dec 8
Blakley Hobbit Campground-RV spot #1
A covered deck with outdoor furniture, a small table, and a grill.

15. 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 CA $705
CA $1,212 total
includes taxes & fees
Nov 24 - Nov 25
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.

16. #3 Blakley Hobbit Campground-Tent spot

#3 Blakley Hobbit Campground-Tent spot
Viola
The price is CA $28
CA $48 total
includes taxes & fees
Nov 8 - Nov 9
#3 Blakley Hobbit Campground-Tent spot
A wooden cabin surrounded by snow-covered trees.

17. 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 CA $195
CA $378 total
includes taxes & fees
Nov 17 - Nov 18
Cabin on the Kickapoo
Two dogs sitting on a grassy field with a pond and trees in the background.

18. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
The price is CA $28
CA $47 total
includes taxes & fees
Dec 5 - Dec 6
#9 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

19. #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 CA $28
CA $48 total
includes taxes & fees
Nov 8 - Nov 9
#8 Blakley Hobbit Campground-Tent spot
A large, multi-story house with a spacious driveway and a well-maintained lawn.

20. Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+

Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+
Camp Douglas
The price is CA $2,990
CA $3,296 total
includes taxes & fees
Nov 11 - Nov 12
Private 35-Acre Resort Near Wisconsin Dells - Indoor Pool, Golf Sim, Sleeps 30+
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

A log cabin interior with a stone fireplace, a sofa, a coffee table, a large bathtub, and a television.
Best Western Park Oasis Inn

Best Western Park Oasis Inn

Best Western Park Oasis Inn
Mauston

10/10 Excellent

Excellent room, clean,breakfast and staff are amazing!Will definitely comeback again and pet friendly!!!!!!100/100
Canada
Rozarene
Reviewed May 24, 2026
Best Western Park Oasis Inn

Find out more about Hillsboro

Everything you need to know about Hillsboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillsboro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsboro. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsboro vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsboro vacation rentals we have selected for you start as low as CA $28 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillsboro rentals

At Expedia, we put the best Hillsboro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hillsboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsboro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.