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Highland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Highland vacation rentals

A bedroom with a large window, a bed, and a view of the outdoors.

1. Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm
Highland
8.0 out of 10, Very good, (2 reviews)
"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
Cheese Wedge Cabin Idyllic Farm
A wooden cabin with a porch, two windows, and a star decoration on the wall.

2. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
$205 nightly
The price is $216
Sep 30 - Oct 1
Total with taxes and fees
River Road Retreat
A playground with various play structures, including a slide, swings, and climbing frames, surrounded by grass and trees.

3. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (37 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveler
$205 nightly
The price is $216
Sep 30 - Oct 1
Total with taxes and fees
River Road Getaway
A log cabin interior with a leather armchair, a sofa, a table with a lamp, and a wood-burning stove.

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.
$183 nightly
The price is $193
Sep 30 - Oct 1
Total with taxes and fees
Crooked Creek - Serenity Cabin
A rustic cabin with a wooden exterior and a red roof, surrounded by a well-maintained grassy area and trees.

5. Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (13 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
$145 nightly
The price is $153
Sep 30 - Oct 1
Total with taxes and fees
Crooked Creek - Relaxation Cabin
A cozy room with a wooden floor, a blue sofa, a door with windows, and a lamp on a table.

6. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (138 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
Oct 4 - Oct 5
Total with taxes and fees
A Comfy Cozy Cottage on Clowney
Living area

7. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (123 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
$204 nightly
The price is $225
Oct 5 - Oct 6
Total with taxes and fees
Serenity Cottage at Mineral Point
A cozy cabin interior with a wooden TV stand, bookshelves, a sofa, and a dining area with chairs.

8. Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
9.6 out of 10, Exceptional, (11 reviews)
"very nice and quiet place to hang your hat."
United States
reuben n.
$162 nightly
The price is $171
Oct 7 - Oct 8
Total with taxes and fees
Crooked Creek - Rustic Cabin
A hallway with wooden flooring, a dark door, and a small table with a vase.

9. 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
$166 nightly
The price is $175
Oct 4 - Oct 5
Total with taxes and fees
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
A cozy living room with a sofa, a patterned rug, and a coffee table. There are three windows with curtains, a lamp, and a door labeled "PRIVATE".

10. 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.
$209 nightly
The price is $231
Oct 11 - Oct 12
Total with taxes and fees
Close to Local Opera House - On the main drag
A spacious living room with a fireplace, wooden flooring, and a large window.

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
9.6 out of 10, Exceptional, (8 reviews)
"Awesome views, clean and Perfect for our 3 couples!"
United States
Cathleen T.
$354 nightly
The price is $373
Oct 12 - Oct 13
Total with taxes and fees
Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point
A bedroom with a bed, a wooden dresser, and a mirror.

12. Cozy 1-bedroom apartment in peaceful Boscobel with AC

Cozy 1-bedroom apartment in peaceful Boscobel with AC
Boscobel
$101 nightly
The price is $112
Sep 30 - Oct 1
Total with taxes and fees
Cozy 1-bedroom apartment in peaceful Boscobel with AC
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 $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?

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.