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Highland Vacation Rentals

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Our top choices for Highland vacation rentals

1. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
The price is CA $252
CA $304 total
includes taxes & fees
Nov 9 - Nov 10
River Road Retreat

2. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (40 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveller
The price is CA $252
CA $304 total
includes taxes & fees
Nov 13 - Nov 14
River Road Getaway

3. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (140 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.
The price is CA $233
CA $346 total
includes taxes & fees
Oct 29 - Oct 30
A Comfy Cozy Cottage on Clowney

4. 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
The price is CA $134
CA $247 total
includes taxes & fees
Oct 27 - Oct 28
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

5. 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.
The price is CA $145
CA $268 total
includes taxes & fees
Nov 3 - Nov 4
Crooked Creek - Serenity Cabin

6. 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.
The price is CA $122
CA $215 total
includes taxes & fees
Nov 15 - Nov 16
Crooked Creek - Relaxation Cabin

7. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (125 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is CA $210
CA $317 total
includes taxes & fees
Oct 27 - Oct 28
Serenity Cottage at Mineral Point

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.
The price is CA $91
CA $333 total
includes taxes & fees
Oct 29 - Oct 30
Close to Local Opera House - On the main drag

9. 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.
The price is CA $137
CA $239 total
includes taxes & fees
Nov 15 - Nov 16
Crooked Creek - Rustic Cabin

10. 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, (14 reviews)
"Awesome views, clean and Perfect for our 3 couples!"
United States
Cathleen T.
The price is CA $392
CA $600 total
includes taxes & fees
Oct 29 - Oct 30
Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point

11. KwikStay: Spacious 5BR Townhome Near Spring Green Golf Course & Park

KwikStay: Spacious 5BR Townhome Near Spring Green Golf Course & Park
Spring Green
9.8 out of 10, Exceptional, (28 reviews)
"The host is a pleasure to work with. The house worked great for our needs. Thank you!"
United States
David A.
The price is CA $402
CA $485 total
includes taxes & fees
Nov 15 - Nov 16
KwikStay: Spacious 5BR Townhome Near Spring Green Golf Course & Park
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Highland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.