Highland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Highland vacation rentals

1 bedroom, iron/ironing board, bed sheets

Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm
Highland
10.0 out of 10, Exceptional, (1 review)
"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
The price is ￥34,470
￥42,440 total
includes taxes & fees
Jun 8 - Jun 9
Cheese Wedge Cabin Idyllic Farm
TV, books

Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (14 reviews)
"Everything from booking, cleanliness, amenities and checking out were excellent. The front porch was wonderful!"
United States
Susan M B.
The price is ￥16,737
￥30,470 total
includes taxes & fees
May 10 - May 11
Crooked Creek - Serenity Cabin
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 ￥31,336
￥37,523 total
includes taxes & fees
May 13 - May 14
River Road Retreat
Interior

A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (123 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.
The price is ￥26,124
￥38,924 total
includes taxes & fees
May 16 - May 17
A Comfy Cozy Cottage on Clowney
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 ￥31,336
￥37,523 total
includes taxes & fees
May 13 - May 14
River Road Getaway
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 ￥25,488
￥37,180 total
includes taxes & fees
May 11 - May 12
Serenity Cottage at Mineral Point
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 ￥50,993
￥85,083 total
includes taxes & fees
May 24 - May 25
Relax with beautiful views overlooking the Wisconsin River
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 ￥13,662
￥24,026 total
includes taxes & fees
May 13 - May 14
Crooked Creek - Relaxation Cabin
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 ￥15,029
￥26,369 total
includes taxes & fees
Jun 8 - Jun 9
Crooked Creek - Rustic Cabin
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 ￥34,443
￥41,627 total
includes taxes & fees
May 27 - May 28
Downtown Spring Green Oasis Steps to Park & Golf
Smart TV

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
10.0 out of 10, Exceptional, (1 review)
"Awesome views, clean and Perfect for our 3 couples!"
United States
Cathleen T.
The price is ￥40,527
￥63,117 total
includes taxes & fees
May 26 - May 27
Escape to this amazing 3 bedroom home just 5 minutes from Historic Mineral Point
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 ￥15,041
￥22,480 total
includes taxes & fees
May 17 - May 18
Charming 3-bedroom upstairs apartment in welcoming Fennimore.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Hotel Reviews

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

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

10/10 Excellent
"The kitchen has every dish you might need to cook, it’s very spacious with indoor and outdoor seating and a beautiful view! Everything was very clean and the host was immediately responsive with any questions that I had throughout the stay! A reminder to anyone going to the tea house outside to check for ticks after but the view is worth it!! "
Brittney 2-night trip
Posted 2 days ago
Elegant country retreat near Spring Green w expansive views of Driftless Region

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

  • View our selection of featured holiday rentals in Highland
  • Use the map to find apartments and other holiday homes in the Highland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland while they last

Look no further and take a look at our great range of rental properties in Highland!

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.