Holiday Rentals in Highland

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Highland

Highland: Driftless Fun Awaits

10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
The price is €208
includes taxes & fees
23 Sept - 24 Sept
Highland: Driftless Fun Awaits

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

10.0 out of 10, Exceptional, (486)
"it was a very relaxing serene location. The home had everything we needed. "
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

Elegant country retreat near Spring Green w expansive views of Driftless Region

10.0 out of 10, Exceptional, (61)
"This house was lovely and very conveniently located to visit local attractions. "
Elegant country retreat near Spring Green w expansive views of Driftless Region

A Comfy Cozy Cottage on Clowney

9.6 out of 10, Exceptional, (111)
"Comfortable, easy stay for a weekend. "
The price is €183
includes taxes & fees
23 Sept - 24 Sept
A Comfy Cozy Cottage on Clowney

The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

10.0 out of 10, Exceptional, (154)
"Great stay with lovely scenery and beautiful cabin. Would highly recommend to anyone."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

Serenity Cottage at Mineral Point

10.0 out of 10, Exceptional, (92)
"What a wonderful place to stay. So much better than a hotel."
The price is €154
includes taxes & fees
23 Sept - 24 Sept
Serenity Cottage at Mineral Point

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

10.0 out of 10, Exceptional, (21)
"Barn was beautiful, clean & fun amenities."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Brigham View

10.0 out of 10, Exceptional, (10)
"Group of friends stayed for the weekend. Awesome house, beautiful views. Beds were very comfy!"
Brigham View

The Guest House

10.0 out of 10, Exceptional, (30)
"Excellent place to stay! "
The Guest House

Relax with beautiful views overlooking the Wisconsin River

10.0 out of 10, Exceptional, (49)
"First annual Memorial Day weekend family getaway. Perfect place for three couples to relax and enjoy the Driftless region. Amazing views of the Wisconsin river and comfortable accommodations."
Relax with beautiful views overlooking the Wisconsin River

Unique! A renovated old railroad depot turned into a cozy cottage.

10.0 out of 10, Exceptional, (120)
"Wonderful stay! Absolutely lovely property. We plan to come back in 2026!"
Unique! A renovated old railroad depot turned into a cozy cottage.

Cozy hillside retreat near trout stream, public forest and UTV trails.

10.0 out of 10, Exceptional, (7)
"Great cabin in a great location. So peaceful and relaxing. We loved our time there and are looking forward to returning!"
Cozy hillside retreat near trout stream, public forest and UTV trails.

Serenity cabin at Crooked Creek

10.0 out of 10, Exceptional, (8)
"the place was peacefull and cozy, had everything we needed for our short stay, we enjoyed the outdoor fire pit a lot, seating outside in the porch with a morning coffee and enjoying the scenery was my highlight."
Serenity cabin at Crooked Creek

Amish-Built Cabin in the Driftless Area

10.0 out of 10, Exceptional, (69)
"Wonderful cabin. Had everything we needed plus everything we might of wanted. "
Amish-Built Cabin in the Driftless Area

River's Edge Cabin, LLC

10.0 out of 10, Exceptional, (81)
"Repeat guest, everything is top notch. Couldn't ask for anything more!"
River's Edge Cabin, LLC

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

9.6 out of 10, Exceptional, (5)
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

10.0 out of 10, Exceptional, (38)
"We enjoyed fishing and the kayaks!"
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville

10.0 out of 10, Exceptional, (3)
"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...
NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville

Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

10.0 out of 10, Exceptional, (45)
"Was a wonderful Valentine’s Day weekend very quiet cozy stay will definitely be staying there again "
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

Relaxation cabin at Crooked Creek

9.6 out of 10, Exceptional, (5)
"Everything smooth and the cabin was very good "
Relaxation cabin at Crooked Creek
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Highland Hotel Reviews

Find out more about Highland

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, apart-hotels, 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 €154 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?

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin: This holiday home rental outside of Highland is located on a river, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What’s there to see and do in Highland?

Beach at Black Hawk Lake Recreation Area and Blackhawk Lake Recreation Area are a couple of lovely local spots to get outside and enjoy nature. Spurgeon Vineyards & Winery and The House on the Rock 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.