Highland Vacation Rentals

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Our top choices for Highland vacation rentals

Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm
Highland
10.0 out of 10, Exceptional, (1 review)
"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
$268 nightly
The price is $270
Jun 1 - Jun 2
Total with taxes and fees
Cheese Wedge Cabin Idyllic Farm

Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (14 reviews)
"Everything from booking, cleanliness, amenities and checking out were excellent. The front porch was wonderful!"
United States
Susan M B.
$183 nightly
The price is $193
May 24 - May 25
Total with taxes and fees
Crooked Creek - Serenity Cabin

Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.6 out of 10, Exceptional, (10 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
$145 nightly
The price is $153
May 17 - May 18
Total with taxes and fees
Crooked Creek - Relaxation Cabin

River Road Retreat

River Road Retreat
Muscoda
9.6 out of 10, Exceptional, (25 reviews)
"Will for sure stay again "
United States
Nicole
$228 nightly
The price is $241
May 18 - May 19
Total with taxes and fees
River Road Retreat

A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (123 reviews)
"The cottage was very quaint and comfortable. Great location for exploring downtown Mineral Point on foot. Had a fun stay."
United States
Rick C.
$225 nightly
The price is $248
May 16 - May 17
Total with taxes and fees
A Comfy Cozy Cottage on Clowney

Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (117 reviews)
"Outstanding property, great location, will stay again."
United States
James S.
$209 nightly
The price is $231
May 19 - May 20
Total with taxes and fees
Serenity Cottage at Mineral Point

River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (30 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveler
$228 nightly
The price is $241
May 18 - May 19
Total with taxes and fees
River Road Getaway

Downtown Spring Green Oasis Steps to Park & Golf

Downtown Spring Green Oasis Steps to Park & Golf
Spring Green
9.8 out of 10, Exceptional, (21 reviews)
"Beautiful spacious home with many amenities! The hot tub was very relaxing. We loved walking around town and being close to unique attractions like House on the Rock and Governor Dodge State Park."
United States
Gabriella C.
$252 nightly
The price is $266
May 18 - May 19
Total with taxes and fees
Downtown Spring Green Oasis Steps to Park & Golf

Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
9.6 out of 10, Exceptional, (8 reviews)
"very nice and quiet place to hang your hat."
United States
reuben n.
$160 nightly
The price is $168
Jun 1 - Jun 2
Total with taxes and fees
Crooked Creek - Rustic Cabin

Relax with beautiful views overlooking the Wisconsin River

Relax with beautiful views overlooking the Wisconsin River
Blue River
10.0 out of 10, Exceptional, (56 reviews)
"Great place to relax and get away. "
United States
Debbie N.
$478 nightly
The price is $504
May 24 - May 25
Total with taxes and fees
Relax with beautiful views overlooking the Wisconsin River

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
10.0 out of 10, Exceptional, (1 review)
"Apartment was big and clean. Check in was super easy! Bed was comfortable and rooms are very spacious. I would definitely stay again if I’m in the area."
United States
DeAnne V.
$136 nightly
The price is $143
May 17 - May 18
Total with taxes and fees
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point

Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (1 review)
"Awesome views, clean and Perfect for our 3 couples!"
United States
Cathleen T.
$381 nightly
The price is $402
May 26 - May 27
Total with taxes and fees
Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point
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 $193 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 The House on the Rock 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.