Highland Vacation Rentals

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Our top choices for Highland vacation rentals

Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (12 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
Feb 15 - Feb 16
Total with taxes and fees
Crooked Creek - Serenity Cabin

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.
$157 nightly
The price is $166
Feb 16 - Feb 17
Total with taxes and fees
Crooked Creek - Rustic Cabin

Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (8 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
$145 nightly
The price is $153
Feb 16 - Feb 17
Total with taxes and fees
Crooked Creek - Relaxation Cabin

A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (121 reviews)
"It was a very nice cottage. We enjoyed the stay! "
United States
james s.
$225 nightly
The price is $248
Feb 16 - Feb 17
Total with taxes and fees
A Comfy Cozy Cottage on Clowney

Close to Local Opera House - On the main drag

Close to Local Opera House - On the main drag
Downtown Mineral Point
9.8 out of 10, Exceptional, (43 reviews)
"Very good location. Apartment was clean, beds were more comfortable than I expected from foam mattresses. Would stay here again !"
United States
Wayne O.
$154 nightly
The price is $170
Feb 15 - Feb 16
Total with taxes and fees
Close to Local Opera House - On the main drag

Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (110 reviews)
"Outstanding property, great location, will stay again."
United States
James S.
$205 nightly
The price is $226
Feb 16 - Feb 17
Total with taxes and fees
Serenity Cottage at Mineral Point

River Road Retreat

River Road Retreat
Muscoda
9.6 out of 10, Exceptional, (24 reviews)
"We had a great stay"
United States
Robert S.
$228 nightly
The price is $241
Feb 15 - Feb 16
Total with taxes and fees
River Road Retreat

River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (29 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
Feb 14 - Feb 15
Total with taxes and fees
River Road Getaway

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
$125 nightly
The price is $132
Feb 16 - Feb 17
Total with taxes and fees
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Hot Tub/Golfing/King Bed @ The Hemlock

Hot Tub/Golfing/King Bed @ The Hemlock
Spring Green
9.8 out of 10, Exceptional, (21 reviews)
"Great house. "
United States
Kathleen B.
$425 nightly
The price is $448
Feb 17 - Feb 18
Total with taxes and fees
Hot Tub/Golfing/King Bed @ The Hemlock
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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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?

Elegant country retreat near Spring Green w expansive views of Driftless Region: 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. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so 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?

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.