Highland Vacation Rentals from $175: Search Short-Term Rentals

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In two months

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Our top choices for Highland vacation rentals

A Comfy Cozy Cottage on Clowney

Mineral Point

Tashia N.

$225 nightly

Jul 21 - Jul 22

Total with taxes and fees

River Road Retreat

Muscoda

Nicole

$228 nightly

Jul 22 - Jul 23

Total with taxes and fees

Crooked Creek - Serenity Cabin

Boscobel

Susan M B.

$183 nightly

Jul 22 - Jul 23

Total with taxes and fees

Crooked Creek - Rustic Cabin

Boscobel

reuben n.

$162 nightly

Jul 28 - Jul 29

Total with taxes and fees

Serenity Cottage at Mineral Point

Mineral Point

Katie K.

$244 nightly

Aug 17 - Aug 18

Total with taxes and fees

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Fennimore

Christina

$166 nightly

Jul 20 - Jul 21

Total with taxes and fees

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

Mineral Point

Cathleen T.

$353 nightly

Jul 20 - Jul 21

Total with taxes and fees

River Road Getaway

Muscoda

Anonymous traveler

$227 nightly

Jul 26 - Jul 27

Total with taxes and fees

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Top Highland Hotel Reviews

Don Q Inn

10/10 Excellent

"Unique! Refreshing and not the run of the mill chain hotel"

Spring Valley Inn

8/10 Good

"The rooms were clean and the beds were great. The shower was brand new. The A/C was in a battle with the heat dome and humidity so the room was cool but a bit damp as happens. The breakfast was nice and they have local beer and other beverage, snack, and even ice cream options. The staff were super helpful and friendly."

AmericInn by Wyndham Dodgeville

10/10 Excellent

"The AmericInn was wonderful. We head to Spring Green every year to American Players Theater. We’d never stayed at this place before and are glad we tried it. The pool was great; salt water pool so no chlorine. Heated perfectly. Breakfast similar to other hotels but not overcooked eggs or sausage. Rooms had been renovated. Newer beds and very comfortable. Kim was at the front desk and also did the breakfast. She made everyone feel like they were home. Engaging and nice. Will defiantly go back next year for our annual 3-night stay."

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

10/10 Excellent

"We really enjoyed our stay! We enjoyed kayaking on lake and looking for turtles from the deck in the evenings. There was plenty of comfortable deck furniture, and my mother even had me look into ordering the lower patio lounge chairs for her at home. The kitchen had everything we need for meals. The ping pong table and games were fun and I now have to get the monopoly deal card game for at home as well. The wall A/C unit worked great and even with temps in the 90s we all slept great. The bedding was very soft and there were a bunch of comfortable throws around the house if you ever got the chills. My brother's dog loved the place (city apartment dog) and enjoyed his first campfire. The beach just down the road at the campsite was nice as well and had life vests for borrowing. My uncle was jealous that he didn't come with when we told him about the larger fish we saw jumping in the lake. There were also plenty of birds if you like bird watching. We went to see House on the Rock, Taliesin (ages 8 only) and went tubing down the Wisconsin River (dogs need to be in canoes if using Wisconsin Riverside Resort). Overall, we really enjoyed ourselves and even though there are neighbors, we couldn't see (trees) or hear anyone else from the deck and so it felt very private."

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 $175 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.

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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?

Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly: This vacation home near Highland offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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?

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 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.

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Check prices for these dates

Our top choices for Highland vacation rentals

A Comfy Cozy Cottage on Clowney

River Road Retreat

Crooked Creek - Serenity Cabin

Crooked Creek - Rustic Cabin

Serenity Cottage at Mineral Point

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

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

River Road Getaway

Close to Local Opera House - On the main drag

Crooked Creek - Relaxation Cabin

Downtown Spring Green Oasis Steps to Park & Golf

Find vacation rentals that suit your style

Top Highland Hotel Reviews

Don Q Inn

Spring Valley Inn

AmericInn by Wyndham Dodgeville

Holiday Inn Express and Suites-Platteville by IHG

Quality Inn & Suites Belmont - Platteville

The Round Barn Lodge

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

Pine Ridge Motel

Napps Motel

Find out more about Highland

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