Highland Vacation Rentals

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Oct 18 - Oct 19
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Oct 31 - Nov 2

Vacation Rentals in Highland

TV
Highland: Driftless Fun Awaits
Highland: Driftless Fun Awaits
10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
Joshua
$245 nightly
The price is $255
Nov 17 - Nov 18
Total with taxes and fees
Highland: Driftless Fun Awaits
Exterior
Rustic Cabin at Crooked Creek
Rustic Cabin at Crooked Creek
9.6 out of 10, Exceptional, (8)
"very nice and quiet place to hang your hat."
reuben n.
$155 nightly
The price is $164
Nov 2 - Nov 3
Total with taxes and fees
Rustic Cabin at Crooked Creek
Exterior
Serenity cabin at Crooked Creek
Serenity cabin at Crooked Creek
10.0 out of 10, Exceptional, (9)
"the place was peacefull and cozy, had everything we needed for our short stay, we enjoyed the outdoor fire pit a lot, seating outside in the porch with a morning coffee and enjoying the scenery was my highlight."
Monica R.
$160 nightly
The price is $169
Oct 30 - Oct 31
Total with taxes and fees
Serenity cabin at Crooked Creek
Exterior detail
Relaxation cabin at Crooked Creek
Relaxation cabin at Crooked Creek
9.8 out of 10, Exceptional, (7)
"Everything smooth and the cabin was very good "
david h.
$146 nightly
The price is $154
Oct 20 - Oct 21
Total with taxes and fees
Relaxation cabin at Crooked Creek
Interior
Suite in the heart of the center of spring green
Suite in the heart of the center of spring green
9.8 out of 10, Exceptional, (92)
"Wonderful place to stay! Clean, welcoming, comfortable--the perfect place to overnight when seeing plays at American Players Theatre."
Jessica L.
$122 nightly
The price is $128
Oct 19 - Oct 20
Total with taxes and fees
Suite in the heart of the center of spring green
Outdoor dining
A Comfy Cozy Cottage on Clowney
A Comfy Cozy Cottage on Clowney
9.6 out of 10, Exceptional, (115)
"Comfortable, easy stay for a weekend. "
Kelly
$188 nightly
The price is $208
Oct 19 - Oct 20
Total with taxes and fees
A Comfy Cozy Cottage on Clowney
Private kitchen
Quaint & Quiet 2 bed 1 bath
Quaint & Quiet 2 bed 1 bath
10.0 out of 10, Exceptional, (1)
"the location was convinience for us considering my brother lives one block away.They were very nice to accommodate a very late check in."
Monica R.
$145 nightly
The price is $153
Oct 19 - Oct 20
Total with taxes and fees
Quaint & Quiet 2 bed 1 bath
Outdoor dining
Serenity Cottage at Mineral Point
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (98)
"What a wonderful place to stay. So much better than a hotel."
Sharon L R.
$160 nightly
The price is $177
Oct 20 - Oct 21
Total with taxes and fees
Serenity Cottage at Mineral Point
Interior
River Road Retreat
River Road Retreat
9.6 out of 10, Exceptional, (18)
"Relaxing trip with family- lived the cabin and the kids loved the basement"
Nora M.
$226 nightly
The price is $238
Oct 19 - Oct 20
Total with taxes and fees
River Road Retreat
Spa
Aunt Happy’s Hideaway: charming 2 bedroom cabin near Mineral Point
Aunt Happy’s Hideaway: charming 2 bedroom cabin near Mineral Point
9.0 out of 10, Wonderful, (9)
"Beautiful location and well kept. Great host communication."
Anonymous traveler
Aunt Happy’s Hideaway: charming 2 bedroom cabin near Mineral Point
Outdoor dining
River Road Getaway
River Road Getaway
9.6 out of 10, Exceptional, (26)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
Anonymous traveler
$226 nightly
The price is $238
Oct 19 - Oct 20
Total with taxes and fees
River Road Getaway
Fridge, microwave, oven, stovetop
Relax with beautiful views overlooking the Wisconsin River
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (51)
"The house was great, we had a very relaxing and fun vacation!"
Wendy B.
Relax with beautiful views overlooking the Wisconsin River
Fridge, microwave, oven, stovetop
Hot Tub/Golfing/King Bed @ The Hemlock
Hot Tub/Golfing/King Bed @ The Hemlock
9.8 out of 10, Exceptional, (19)
"The Hemlock was perfect for our family. We were visiting Spring Green for a family wedding and enjoyed all the clean space and fully equipped kitchen. We also had fun riding the electric bikes. Will definitely stay here on our next visit!"
Charla S.
$317 nightly
The price is $334
Oct 21 - Oct 22
Total with taxes and fees
Hot Tub/Golfing/King Bed @ The Hemlock
Fireplace
Historic District, Charming Cottage, Sleeps 10
Historic District, Charming Cottage, Sleeps 10
2.0 star property
10.0 out of 10, Exceptional, (1)
$341 nightly
The price is $345
Oct 19 - Oct 20
Total with taxes and fees
Historic District, Charming Cottage, Sleeps 10
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

Deer Valley Lodge & Golf

Deer Valley Lodge & Golf

10/10 Excellent
"Great experience with everything, we will definitely be back!"
Brianna 1-night trip
Posted 4 days ago
Deer Valley Lodge & Golf

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 $128 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?

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!: This vacation home rental near Highland is located on a river and has an indoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. It has 6 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.