Highland Vacation Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Highland vacation rentals

Smart TV, fireplace, books, stereo

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, (44 reviews)
"Super cute, spacious, convenient location. Excellent communication from host. The area has a lot to do & we wish we had stayed longer!"
United States
Amy '.
Close to Local Opera House - On the main drag
TV, books

Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (13 reviews)
"Everything from booking, cleanliness, amenities and checking out were excellent. The front porch was wonderful!"
United States
Susan M B.
The price is R$ 534
R$ 966 total
includes taxes & fees
4 May - 5 May
Crooked Creek - Serenity Cabin
Smart TV, fireplace

Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (117 reviews)
"Outstanding property, great location, will stay again."
United States
James S.
The price is R$ 812
R$ 1.184 total
includes taxes & fees
5 May - 6 May
Serenity Cottage at Mineral Point
Exterior

River Road Retreat

River Road Retreat
Muscoda
9.6 out of 10, Exceptional, (25 reviews)
"Will for sure stay again "
United States
Nicole
The price is R$ 995
R$ 1.191 total
includes taxes & fees
3 May - 4 May
River Road Retreat
TV

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 R$ 488
R$ 849 total
includes taxes & fees
12 May - 13 May
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, (123 reviews)
"This little house is a treasure. We loved staying there, and even on a subzero night it was cozy."
United States
Susan M.
The price is R$ 828
R$ 1.234 total
includes taxes & fees
8 May - 9 May
A Comfy Cozy Cottage on Clowney
Property grounds

Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.6 out of 10, Exceptional, (10 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
The price is R$ 436
R$ 766 total
includes taxes & fees
17 May - 18 May
Crooked Creek - Relaxation Cabin
Children's area

River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (30 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveler
The price is R$ 995
R$ 1.191 total
includes taxes & fees
3 May - 4 May
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)
"Beautiful spacious home with many amenities! The hot tub was very relaxing. We loved walking around town and being close to unique attractions like House on the Rock and Governor Dodge State Park."
United States
Gabriella C.
The price is R$ 1.093
R$ 1.322 total
includes taxes & fees
20 May - 21 May
Downtown Spring Green Oasis Steps to Park & Golf
Interior

Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
10.0 out of 10, Exceptional, (1 review)
"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.
The price is R$ 478
R$ 714 total
includes taxes & fees
3 May - 4 May
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
3 bedrooms, free WiFi, bed sheets

Relax with beautiful views overlooking the Wisconsin River

Relax with beautiful views overlooking the Wisconsin River
Blue River
10.0 out of 10, Exceptional, (56 reviews)
"Great place to relax and get away. "
United States
Debbie N.
The price is R$ 1.617
R$ 2.682 total
includes taxes & fees
24 May - 25 May
Relax with beautiful views overlooking the Wisconsin River
Living area

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
The price is R$ 1.276
R$ 1.992 total
includes taxes & fees
3 May - 4 May
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.
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Top Highland Hotel Reviews

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

10/10 Excellent
"This cabin was exactly what we needed. There’s something so restorative about the silence of the Driftless; without the noise of city life, you’re left with nothing but the peaceful sounds of nature. We left feeling completely recharged and are already dreaming of our next escape to this hidden gem"
Angela O. 4-night trip
Posted 1 day ago
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

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’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.