Highland Vacation Rentals

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Vacation Rentals in Highland

Highland: Driftless Fun Awaits

Highland
10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
United States
Joshua
$225 nightly
The price is $234
Nov 17 - Nov 18
Total with taxes and fees
Highland: Driftless Fun Awaits

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

Avoca
10.0 out of 10, Exceptional, (496)
"Another great stay at this awesome house!"
United States
William J.
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

Serenity Cottage at Mineral Point

Mineral Point
10.0 out of 10, Exceptional, (99)
"Cozy home with good beds and kitchen"
United States
Claudia W.
$176 nightly
The price is $194
Nov 17 - Nov 18
Total with taxes and fees
Serenity Cottage at Mineral Point

River Road Retreat

Muscoda
9.6 out of 10, Exceptional, (21)
"Loved the place. Very clean & cozy. We go back to stay "
United States
Christy G.
$226 nightly
The price is $238
Nov 15 - Nov 16
Total with taxes and fees
River Road Retreat

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

Spring Green
10.0 out of 10, Exceptional, (67)
"The property and house are breathtaking. We particularly loved the Tea House. Gorgeous, clean and the host was wonderful and responsive. A great place to stay!"
United States
Paul D.
Elegant country retreat near Spring Green w expansive views of Driftless Region

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

Arena
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

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

Richland Center
10.0 out of 10, Exceptional, (160)
"Great stay with lovely scenery and beautiful cabin. Would highly recommend to anyone."
United States
Jacob H.
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

Luxury Retreat in Prime Downtown Spring Green Location

Spring Green
10.0 out of 10, Exceptional, (58)
"The location was perfect with restaurants and bars right across the street. Farmers market on Saturday morning. Comfortable bed and updated bathroom were appreciated. We will stay there again!"
United States
Michael M.
Luxury Retreat in Prime Downtown Spring Green Location

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

Arena
9.8 out of 10, Exceptional, (7)
"Our stay was perfect. More than enough amenities and fine finishes. Kyle & Erin are very responsive and great hosts. Our stay could not have been better. "
United States
John M.
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

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

Avoca
9.8 out of 10, Exceptional, (45)
"We had a lovely time. Old friends, great memories. Loved the setting, peace and quiet. The deck was great. So glad to have bedrooms on the same level. Hoping to come back next summer"
United States
Jo S.
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI

Lone Rock
9.8 out of 10, Exceptional, (91)
"Lovely old farm house with lots of character in the beautiful Driftless area."
United States
Darlene M.
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI

Downtown's Best View at Howdle's Retreat

Downtown Mineral Point
9.6 out of 10, Exceptional, (12)
"Great to visit Mineral Point "
United States
Stuart S.
Downtown's Best View at Howdle's Retreat

Brigham View

Barneveld
10.0 out of 10, Exceptional, (14)
"A great place to stay for access to the driftless area of Wisconsin. Stayed here and fished a lot of the local streams for trout. The place was very clean, and felt like home. Recommend trying the Hi Point steakhouse if you’re in the area. Great food and cocktails. Beautiful sunrises and sunsets also a big plus."
United States
Dale R.
Brigham View

A Comfy Cozy Cottage on Clowney

Mineral Point
9.6 out of 10, Exceptional, (118)
"Comfortable, easy stay for a weekend. "
United States
Kelly
$189 nightly
The price is $209
Nov 16 - Nov 17
Total with taxes and fees
A Comfy Cozy Cottage on Clowney

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

Dodgeville
9.6 out of 10, Exceptional, (5)
"Everything was perfect. The place was recently remodeled and had many very nice touches. We were able to relax and enjoy a cup of coffee on the deck every morning, taking in the lovely wildflower landscape. The house accommodated the different sleep schedules- those of us who wanted an early night had no problem with folks talking and/or watching tv upstairs. The interior has some fun decor for movie and TV buffs, and some nice, playful art pieces all around. Beds very comfy, plenty of fresh...
United States
Beth G.
NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville

Serenity cabin at Crooked Creek

Boscobel
10.0 out of 10, Exceptional, (11)
"This cabin was everything I was looking for in a 3 day fishing trip. Located in a quiet hollow with lots of wildlife and only 15 minutes from great trout streams. It was quaint, but we did not spend much time inside. Check in/out was a breeze. I’ll be keeping this cabin in mind if I return to the Wisconsin Driftless. "
United States
Will C.
$165 nightly
The price is $174
Nov 30 - Dec 1
Total with taxes and fees
Serenity cabin at Crooked Creek

Relax with beautiful views overlooking the Wisconsin River

Blue River
10.0 out of 10, Exceptional, (53)
"The house was great, we had a very relaxing and fun vacation!"
United States
Wendy B.
$372 nightly
The price is $392
Dec 1 - Dec 2
Total with taxes and fees
Relax with beautiful views overlooking the Wisconsin River

Quaint & Quiet 2 bed 1 bath

Fennimore
10.0 out of 10, Exceptional, (1)
"the location was convinience for us considering my brother lives one block away.They were very nice to accommodate a very late check in."
United States
Monica R.
$145 nightly
The price is $153
Nov 15 - Nov 16
Total with taxes and fees
Quaint & Quiet 2 bed 1 bath

Hot Tub/Golfing/King Bed @ The Hemlock

Spring Green
9.8 out of 10, Exceptional, (20)
"Great house. "
United States
Kathleen B.
$277 nightly
The price is $292
Dec 14 - Dec 15
Total with taxes and fees
Hot Tub/Golfing/King Bed @ The Hemlock

The Guest House

Boscobel
10.0 out of 10, Exceptional, (32)
"It was everything they said and more. Great hosts. Comfortable beds, quiet, farmhouse setting. Highly recommended!!"
United States
Shari C.
The Guest House
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 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 Highland 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 Highland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Highland 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 $153 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 Highland rentals

At Expedia, we put the best Highland 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 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 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 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 vacation rental in Highland?

Yes, we have vacation rentals near well known local attractions in Highland, or you can go with a more secluded option if you want a relaxing place to stay. Highland is known for its parks.

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

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin: This vacation home rental near Highland is located on a river and has a fireplace, a patio, and a barbecue grill 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 vacation with amenities like 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 Whispering Winds Winery are a couple of places you'll find in the larger area.

What’s a vacation rental in Highland like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Highland. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.