Highland Holiday Rentals

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Our top choices for Highland holiday rentals

Apartment in Highland

Highland: Driftless Fun Awaits
10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
United States
Joshua
Highland: Driftless Fun Awaits
10.0 out of 10, Exceptional, (1)
"If you are looking for a unconventional place to unplug and unwind, the Cheese Wedge Cabin is a charming getway. Etienne is a lovely host who made us feel welcome and comfortable on her farm. We got up close and personal with the sheep, chickens, and Phoenix the sheepdog (who is the gentlest giant and steadfast companion). We had plenty of privacy in the cabin while still being close enough to get anything we needed from the private guest kitchen & bath connected to the main house. Another...
United States
Annie
Cheese Wedge Cabin Idyllic Farm
10.0 out of 10, Exceptional, (70)
"Wonderful house in a beautiful setting! Highly recommend!"
United States
Malahn D.
Elegant country retreat near Spring Green w expansive views of Driftless Region
10.0 out of 10, Exceptional, (500)
"Another great stay at this awesome house!"
United States
William J.
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
9.8 out of 10, Exceptional, (7)
"Perfect spot for a family getaway"
United States
Steve M.
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
10.0 out of 10, Exceptional, (160)
"We were very happy with the amenities and the scenery "
United States
Dale M.
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
9.6 out of 10, Exceptional, (22)
"Barn was beautiful, clean & fun amenities."
United States
Kerry S.
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Cottage in Mineral Point

A Comfy Cozy Cottage on Clowney
9.6 out of 10, Exceptional, (118)
"Comfortable, easy stay for a weekend. "
United States
Kelly
The price is AU$378
includes taxes & fees
17 Dec - 18 Dec
A Comfy Cozy Cottage on Clowney

Holiday Home in Mineral Point

Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (103)
"Outstanding property, great location, will stay again."
United States
James S.
The price is AU$351
includes taxes & fees
11 Dec - 12 Dec
Serenity Cottage at Mineral Point
9.8 out of 10, Exceptional, (45)
"We enjoyed fishing and the kayaks!"
United States
Teala B.
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

Cabin in Muscoda

River Road Retreat
9.6 out of 10, Exceptional, (23)
"Loved the place. Very clean & cozy. We go back to stay "
United States
Christy G.
The price is AU$363
includes taxes & fees
15 Dec - 16 Dec
River Road Retreat

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.
Close to Local Opera House - On the main drag

Holiday Home in Barneveld

Brigham View
10.0 out of 10, Exceptional, (14)
"Our second stay while in the area with family to attend American Players Theater events. Love the views, amazing accommodations, and extremely responsive owners! "
United States
Sarah D.
Brigham View

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 AU$445
includes taxes & fees
14 Dec - 15 Dec
Hot Tub/Golfing/King Bed @ The Hemlock

Apartment in Boscobel

The Guest House
10.0 out of 10, Exceptional, (32)
"Excellent place to stay! "
United States
Paul B.
The Guest House
10.0 out of 10, Exceptional, (11)
"Everything from booking, cleanliness, amenities and checking out were excellent. The front porch was wonderful!"
United States
Susan M B.
The price is AU$288
includes taxes & fees
11 Dec - 12 Dec
Crooked Creek - Serenity Cabin

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 AU$363
includes taxes & fees
11 Dec - 12 Dec
River Road Getaway
10.0 out of 10, Exceptional, (125)
"It was cute and historically decorated!"
United States
Eleanor S.
Unique! A renovated old railroad depot turned into a cozy cottage.
9.8 out of 10, Exceptional, (91)
"Beautiful historic house with lots of space. This house is ideal for families celebrating any and every holiday. The decor and furnishings provide a warm nostalgic feeling along with all the comfort one could want."
United States
Violet R.
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
9.8 out of 10, Exceptional, (6)
"The location was handy and the property was exceptional. Beds were comfortable and the living room is a great space to gather for games, movies or relax with a book. The kitchen had everything we needed and there is ample dining space for larger groups, inside or on the deck. We made use of the fire pit and very clean grill and watched the fireflies at night. It’s very quiet, private and clean. Towels and linens provided were high quality. The host was very thoughtful and communicative. Our...
United States
Sonja H.
NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville
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 favourite 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 depend 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 AU$288 per night. Entering your travel dates in the search wizard might find you 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.