Default HTG hotel image

Highland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Highland vacation rentals

1 bedroom, iron/ironing board, bed sheets

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
$269 nightly
The price is $271
Jul 19 - Jul 20
Total with taxes and fees
Cheese Wedge Cabin Idyllic Farm
Property grounds

Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (11 reviews)
"Very cute cabin in a peaceful setting. Cozy place to lay your head after a long day. Much to do and see in the area. Host was very responsive to any issues that arise, and quick to fix any problems. Will be recommending to family and friends!"
United States
Rosebrad
$145 nightly
The price is $153
Jul 5 - Jul 6
Total with taxes and fees
Crooked Creek - Relaxation Cabin
TV, books

Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (16 reviews)
"The space was amazing! Very clean and cozy. We got some much needed r & r. "
United States
Virginia W.
$183 nightly
The price is $193
Jul 5 - Jul 6
Total with taxes and fees
Crooked Creek - Serenity Cabin
TV

Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
9.6 out of 10, Exceptional, (9 reviews)
"very nice and quiet place to hang your hat."
United States
reuben n.
$162 nightly
The price is $171
Jul 6 - Jul 7
Total with taxes and fees
Crooked Creek - Rustic Cabin
Interior

A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (128 reviews)
"An beautiful home with an interesting history right by the lovely downtown. We thoroughly enjoyed our stay, as we felt welcome and comfortable."
United States
Tashia N.
$224 nightly
The price is $247
Jul 5 - Jul 6
Total with taxes and fees
A Comfy Cozy Cottage on Clowney
Interior

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
8.8 out of 10, Excellent, (3 reviews)
"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
Jul 2 - Jul 3
Total with taxes and fees
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Exterior

River Road Retreat

River Road Retreat
Muscoda
9.6 out of 10, Exceptional, (25 reviews)
"Will for sure stay again "
United States
Nicole
$227 nightly
The price is $239
Jul 6 - Jul 7
Total with taxes and fees
River Road Retreat
Children's area

River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (32 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveler
$227 nightly
The price is $239
Jul 5 - Jul 6
Total with taxes and fees
River Road Getaway
Fridge, microwave, oven, stovetop

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)
"This was a nice stay for us. House is in a nice, quiet neighborhood."
United States
Gretchen P.
$265 nightly
The price is $279
Jul 26 - Jul 27
Total with taxes and fees
Downtown Spring Green Oasis Steps to Park & Golf
Smart TV

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, (2 reviews)
"Awesome views, clean and Perfect for our 3 couples!"
United States
Cathleen T.
$352 nightly
The price is $371
Jul 5 - Jul 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Hotel Reviews

Best Western Dodgeville Inn & Suites

Best Western Dodgeville Inn & Suites

10/10 Excellent
"the staff was had me checked in fast, room was clean and the breakfast was good"
William 1-night trip
Posted 5 hours ago
Best Western Dodgeville Inn & Suites

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.

Explore a world of travel with Expedia

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 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?

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.