Hillsboro Vacation Rentals from $33: Search Short-Term Rentals

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Nov 27 - Nov 29

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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

Tammy

$195 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Wonewoc

Denise L.

$235 nightly

Nov 12 - Nov 13

Total with taxes and fees

A riverside park with a wooden bench, trees, and a grassy area.

3. Blakley Hobbit Large Cabin

Viola

Rebecca B.

$152 nightly

Nov 12 - Nov 13

Total with taxes and fees

Two dogs sitting on a grassy field with a pond and trees in the background.

4. Blakley Hobbit Campground-RV spot #4

Viola

Paul K.

$62 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Viola

joe

$107 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

Reedsburg

Kerri M.

$254 nightly

Nov 17 - Nov 18

Total with taxes and fees

7. 6 Bedroom Home in Gods Country

Wilton

Rambabu

$641 nightly

Nov 12 - Nov 13

Total with taxes and fees

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!

Lyndon Station

Eukesha

$289 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

New Lisbon

Tricia C.

$315 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Viola

Scott C.

$283 nightly

Nov 12 - Nov 13

Total with taxes and fees

11. #4 Blakley Hobbit Campground-Tent spot

Viola

Luke S.

$32 nightly

Nov 12 - Nov 13

Total with taxes and fees

A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

12. Your adventure begins the second you arrive!

Norwalk

Betsy D.

$183 nightly

Nov 18 - Nov 19

Total with taxes and fees

13. #10 Blakley Hobbit Campground-Tent spot

Viola

Huan B.

$32 nightly

Nov 12 - Nov 13

Total with taxes and fees

14. Blakley Hobbit Campground-RV spot #1

Viola

Paul K.

$62 nightly

Nov 12 - Nov 13

Total with taxes and fees

A covered deck with outdoor furniture, a small table, and a grill.

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

Norwalk

Dawn C.

$813 nightly

Nov 24 - Nov 25

Total with taxes and fees

16. #3 Blakley Hobbit Campground-Tent spot

Viola

$32 nightly

Nov 12 - Nov 13

Total with taxes and fees

A wooden cabin surrounded by snow-covered trees.

17. Cabin on the Kickapoo

Readstown

Sujhey B.

$254 nightly

Nov 16 - Nov 17

Total with taxes and fees

18. #9 Blakley Hobbit Campground-Tent spot

Viola

$32 nightly

Nov 12 - Nov 13

Total with taxes and fees

19. #8 Blakley Hobbit Campground-Tent spot

Viola

Nicholas B.

$32 nightly

Nov 12 - Nov 13

Total with taxes and fees

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+

Camp Douglas

$2,246 nightly

Nov 16 - Nov 17

Total with taxes and fees

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Find vacation rentals that suit your style

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

Mauston

10/10 Excellent

Our stay was exceptional! A little bio on us, we are well traveled (USA, Europe and the Caribbean) we prefer to stay at boutique hotels, and away from the crowds. We do extensive research before making our decisions. Based on our criteria; travel dates, hotel and room type, location, and budget we decided to stay here. We (four adults) arrived a little earlier than the 3:00PM check-in. Julie greeted us at the front desk and checked us in promptly. She did not even mention the time nor did she...

Anonymous traveler

A modern bathroom with a large bathtub, a flat-screen TV, and a wooden vanity.

Quality Inn Mauston I-90

Mauston

10/10 Excellent

We went up to the Adams area for the closing weekend of deer hunting season. The hotel was just right. Great pool, great hot tub, perfect after a long day's hunt! The rooms were small, but clean and well maintained. The entire hotel staff was friendly. Breakfast ended at 9am during the week, and they broke it down, even though the room was full of people. They should let it go until people are finished. But everyone was very friendly and helpful!

Roger

A hotel room with a large bed, a separate bathroom with a bathtub, a large mirror, and a television in the corner.

Ramada by Wyndham Richland Center

Richland Center

10/10 Excellent

Anonymous traveler

A modern hotel room with a large bed, a separate sofa, a bathtub, and a flat-screen TV mounted on the wall.

AmericInn by Wyndham Reedsburg

Reedsburg

10/10 Excellent

Donna

A cozy wooden cabin with a balcony overlooking a lush green landscape.

Justin Trails Resort, LLC.

Sparta

10/10 Excellent

Anonymous traveler

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Hillsboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $33 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.