Highland Vacation Rentals

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Our top choices for Highland vacation rentals

Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (12 reviews)
"Everything from booking, cleanliness, amenities and checking out were excellent. The front porch was wonderful!"
United States
Susan M B.
The price is CA $142
CA $258 total
includes taxes & fees
Feb 12 - Feb 13
Crooked Creek - Serenity Cabin

Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
9.6 out of 10, Exceptional, (8 reviews)
"very nice and quiet place to hang your hat."
United States
reuben n.
The price is CA $128
CA $227 total
includes taxes & fees
Feb 10 - Feb 11
Crooked Creek - Rustic Cabin

Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (8 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
The price is CA $119
CA $210 total
includes taxes & fees
Feb 10 - Feb 11
Crooked Creek - Relaxation Cabin

A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (121 reviews)
"It was a very nice cottage. We enjoyed the stay! "
United States
james s.
The price is CA $228
CA $336 total
includes taxes & fees
Feb 10 - Feb 11
A Comfy Cozy Cottage on Clowney

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, (43 reviews)
"Very good location. Apartment was clean, beds were more comfortable than I expected from foam mattresses. Would stay here again !"
United States
Wayne O.
The price is CA $89
CA $242 total
includes taxes & fees
Feb 10 - Feb 11
Close to Local Opera House - On the main drag

Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (109 reviews)
"Outstanding property, great location, will stay again."
United States
James S.
The price is CA $205
CA $299 total
includes taxes & fees
Feb 10 - Feb 11
Serenity Cottage at Mineral Point

River Road Retreat

River Road Retreat
Muscoda
9.6 out of 10, Exceptional, (24 reviews)
"We had a great stay"
United States
Robert S.
The price is CA $274
CA $329 total
includes taxes & fees
Feb 10 - Feb 11
River Road Retreat

River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (29 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveller
The price is CA $274
CA $329 total
includes taxes & fees
Feb 10 - Feb 11
River Road Getaway

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
The price is CA $115
CA $179 total
includes taxes & fees
Feb 10 - Feb 11
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Hot Tub/Golfing/King Bed @ The Hemlock

Hot Tub/Golfing/King Bed @ The Hemlock
Spring Green
9.8 out of 10, Exceptional, (21 reviews)
"Great house. "
United States
Kathleen B.
The price is CA $324
CA $398 total
includes taxes & fees
Feb 22 - Feb 23
Hot Tub/Golfing/King Bed @ The Hemlock
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 rental 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?

Beach at Black Hawk Lake Recreation Area and Blackhawk 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.