Highland Holiday Rentals

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Our top choices for Highland holiday rentals

Apartment in Downtown Mineral Point

Close to Local Opera House - On the main drag
9.8 out of 10, Exceptional, (41)
"Perfect located close to Opera House "
United States
B C.
The price is NZ$303
includes taxes & fees
19 Jan - 20 Jan 2026
Close to Local Opera House - On the main drag
10.0 out of 10, Exceptional, (12)
"Everything from booking, cleanliness, amenities and checking out were excellent. The front porch was wonderful!"
United States
Susan M B.
The price is NZ$323
includes taxes & fees
30 Dec - 31 Dec
Crooked Creek - Serenity Cabin
9.6 out of 10, Exceptional, (8)
"It was a beautiful, solidly built, cozy cabin in a very pretty location. Perfect getaway spot. Very kind and helpful host! "
United States
Lindsay W.
The price is NZ$272
includes taxes & fees
6 Jan - 7 Jan 2026
Crooked Creek - Rustic Cabin

Holiday Home in Mineral Point

Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (104)
"Outstanding property, great location, will stay again."
United States
James S.
The price is NZ$354
includes taxes & fees
29 Dec - 30 Dec
Serenity Cottage at Mineral Point
9.8 out of 10, Exceptional, (8)
"The property was very comfortable and quiet and nicely decorated. I loved our stay and would choose a relaxation cabin again."
United States
Constance L.
The price is NZ$263
includes taxes & fees
29 Dec - 30 Dec
Crooked Creek - Relaxation Cabin

Cottage in Mineral Point

A Comfy Cozy Cottage on Clowney
9.6 out of 10, Exceptional, (118)
"Great location two blocks off main street. Really neat old house with everything you need, we would definitely stay again!!"
United States
Jeff B.
The price is NZ$425
includes taxes & fees
29 Dec - 30 Dec
A Comfy Cozy Cottage on Clowney

Holiday Home in Spring Green

Hot Tub/Golfing/King Bed @ The Hemlock
9.8 out of 10, Exceptional, (21)
"Great house. "
United States
Kathleen B.
The price is NZ$500
includes taxes & fees
18 Jan - 19 Jan 2026
Hot Tub/Golfing/King Bed @ The Hemlock

Cabin in Muscoda

River Road Retreat
9.6 out of 10, Exceptional, (24)
"Wonderful place to stay. Hosts were amazing."
United States
Mary M.
The price is NZ$408
includes taxes & fees
28 Dec - 29 Dec
River Road Retreat
The price is NZ$289
includes taxes & fees
25 Jan - 26 Jan 2026
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
9.2 out of 10, Wonderful, (13)
"Check in and host were awesome. Very peaceful and relaxing"
United States
Theresa H.
The price is NZ$500
includes taxes & fees
31 Dec - 1 Jan 2026
Aunt Happy’s Hideaway: charming 2 bedroom cabin near Mineral Point

Holiday Home in Muscoda

River Road Getaway
9.6 out of 10, Exceptional, (29)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveller
The price is NZ$403
includes taxes & fees
27 Dec - 28 Dec
River Road Getaway
10.0 out of 10, Exceptional, (55)
"The house was great, we had a very relaxing and fun vacation!"
United States
Wendy B.
The price is NZ$863
includes taxes & fees
27 Dec - 28 Dec
Relax with beautiful views overlooking the Wisconsin River
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 Highland Hotel Reviews

Find out more about Highland

Everything you need to know about Highland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland holiday rental for you. At Expedia, you can take your pick from private holiday 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 Highland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. 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 Highland holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland holiday rentals we have selected for you start as low as NZ$303 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland holiday 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 Highland 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 Highland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. 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 a holiday rental in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Highland is known for its parks.

What are some of the best holiday rentals that Highland has to offer?

Elegant country retreat near Spring Green w expansive views of Driftless Region: This holiday home rental outside of Highland is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Highland?

Blackhawk Lake Recreation Area and Beach at Black Hawk Lake Recreation Area are a couple of lovely local spots to get outside and enjoy nature. Spurgeon Vineyards & Winery and Whispering Winds Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Highland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.