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Highland Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Highland vacation rentals

A rustic wooden cabinet with drawers and shelves, a hanging towel, and a chalkboard sign on the wall.

1. Highland: Driftless Fun Awaits

Highland: Driftless Fun Awaits
Highland
10.0 out of 10, Exceptional, (1 review)
"Great property. Had everything we needed. Highly recommend. "
United States
Joshua
$199 nightly
The price is $207
Dec 7 - Dec 8
Total with taxes and fees
Highland: Driftless Fun Awaits
A grassy area with picnic tables and a small cabin.

2. Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (14 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
$141 nightly
The price is $149
Nov 15 - Nov 16
Total with taxes and fees
Crooked Creek - Relaxation Cabin
A wooden cabin with a porch, two windows, and a star decoration on the wall.

3. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"Nice little place with a good location near the river."
United States
matthew g.
$196 nightly
The price is $207
Nov 15 - Nov 16
Total with taxes and fees
River Road Retreat
A wooden porch with two chairs and a table, a 'WELCOME' sign, and a view of a green landscape.

4. Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (16 reviews)
"Worked well for our 2-day stay. "
United States
John V.
$180 nightly
The price is $190
Nov 29 - Nov 30
Total with taxes and fees
Crooked Creek - Serenity Cabin
A wooden deck with two chairs and a table, a welcome sign, and a view of the surrounding greenery.

5. Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
9.6 out of 10, Exceptional, (13 reviews)
"very nice and quiet place to hang your hat."
United States
reuben n.
$160 nightly
The price is $169
Nov 15 - Nov 16
Total with taxes and fees
Crooked Creek - Rustic Cabin
A wooden cabin with a deck, a door, and a star decoration.

6. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (42 reviews)
"Had everything we needed."
United States
Tawnia
$196 nightly
The price is $207
Nov 15 - Nov 16
Total with taxes and fees
River Road Getaway
A hallway with wooden flooring, a dark door, and a small table with a vase.

7. Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
9.4 out of 10, Exceptional, (6 reviews)
"The property was exactly as described. The decor was super cute and the beds were very comfortable! Highly recommend this property!"
United States
Christina
$159 nightly
The price is $168
Nov 17 - Nov 18
Total with taxes and fees
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
A room with a blue sofa, a patterned armchair, a red and gold rug, and a ceiling with intricate designs.

8. 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, (45 reviews)
"Great spot in town. Very nice space."
United States
Rebecca S.
$201 nightly
The price is $222
Nov 15 - Nov 16
Total with taxes and fees
Close to Local Opera House - On the main drag
A cozy living room with a fireplace, wooden beams, a sofa, and a television.

9. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (142 reviews)
"This is such a charming and unique old place, and right next to downtown. What a perfect location in one of the most charming and welcoming towns you'll ever visit!"
United States
Cindy P.
$204 nightly
The price is $225
Nov 15 - Nov 16
Total with taxes and fees
A Comfy Cozy Cottage on Clowney
A wooden deck with a table and chairs, surrounded by a metal fence.

10. Serenity Chalet in Mineral Point

Serenity Chalet in Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (127 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
$228 nightly
The price is $252
Dec 1 - Dec 2
Total with taxes and fees
Serenity Chalet in Mineral Point
A modern house with a covered patio area, large windows, and outdoor furniture.

11. 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
9.4 out of 10, Exceptional, (18 reviews)
"Awesome views, clean and Perfect for our 3 couples!"
United States
Cathleen T.
$368 nightly
The price is $388
Nov 16 - Nov 17
Total with taxes and fees
Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point
An outdoor patio area with string lights, a fire pit, and outdoor furniture.

12. Downtown Spring Green Oasis | Hot Tub & Fire Pit

Downtown Spring Green Oasis | Hot Tub & Fire Pit
Spring Green
9.8 out of 10, Exceptional, (29 reviews)
"Kids loved all the board games and comfy seating options in the living room! Very comfortable stay."
United States
Elizabeth N.
$312 nightly
The price is $329
Nov 15 - Nov 16
Total with taxes and fees
Downtown Spring Green Oasis | Hot Tub & Fire Pit
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

The Round Barn Lodge

The Round Barn Lodge

10/10 Excellent
"Clean room, friendly staff, nice room"
River 1-night trip
Posted 5 hours ago
The Round Barn Lodge

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 $149 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?

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