Highland Holiday Rentals

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Holiday Rentals in Highland

Highland: Driftless Fun Awaits
10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
United States
Joshua
The price is AU$397
includes taxes & fees
18 Nov - 19 Nov
Highland: Driftless Fun Awaits
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
10.0 out of 10, Exceptional, (493)
"Exquisite cabin. This was our fourth stay and it is always very well maintained, providing a great place to get away and recharge. "
United States
JymAndLisa P.
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Elegant country retreat near Spring Green w expansive views of Driftless Region
10.0 out of 10, Exceptional, (64)
"This house was lovely and very conveniently located to visit local attractions. "
United States
Lindsay R.
Elegant country retreat near Spring Green w expansive views of Driftless Region
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
9.6 out of 10, Exceptional, (22)
"Barn was beautiful, clean & fun amenities."
United States
Kerry S.
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (98)
"What a wonderful place to stay. So much better than a hotel."
United States
Sharon L R.
The price is AU$276
includes taxes & fees
26 Oct - 27 Oct
Serenity Cottage at Mineral Point
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
9.6 out of 10, Exceptional, (5)
"Our stay was perfect. More than enough amenities and fine finishes. Kyle & Erin are very responsive and great hosts. Our stay could not have been better. "
United States
John M.
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
10.0 out of 10, Exceptional, (157)
"Great cabin in a beautiful location! Both secluded and very comfortable."
United States
R J.
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
9.6 out of 10, Exceptional, (90)
"Lovely old farm house with lots of character in the beautiful Driftless area."
United States
Darlene M.
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
Suite in the heart of the center of spring green
9.8 out of 10, Exceptional, (93)
"Wonderful place to stay! Clean, welcoming, comfortable--the perfect place to overnight when seeing plays at American Players Theatre."
United States
Jessica L.
The price is AU$201
includes taxes & fees
27 Oct - 28 Oct
Suite in the heart of the center of spring green
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."
United States
Monica R.
The price is AU$263
includes taxes & fees
30 Oct - 31 Oct
Serenity cabin at Crooked Creek
A Comfy Cozy Cottage on Clowney
9.6 out of 10, Exceptional, (117)
"Comfortable, easy stay for a weekend. "
United States
Kelly
The price is AU$324
includes taxes & fees
28 Oct - 29 Oct
A Comfy Cozy Cottage on Clowney
Luxury Retreat in Prime Downtown Spring Green Location
10.0 out of 10, Exceptional, (55)
"Host was very responsive and friendly and the location cannot be beat."
United States
Brian B.
Luxury Retreat in Prime Downtown Spring Green Location
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
9.8 out of 10, Exceptional, (41)
"We enjoyed fishing and the kayaks!"
United States
Teala B.
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (52)
"The house was great, we had a very relaxing and fun vacation!"
United States
Wendy B.
Relax with beautiful views overlooking the Wisconsin River
Spacious Cabin on the Wisconsin River!
9.6 out of 10, Exceptional, (28)
"The property is beautiful and very comfortable. "
United States
Tina C.
Spacious Cabin on the Wisconsin River!
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
9.8 out of 10, Exceptional, (48)
"Was a wonderful Valentine’s Day weekend very quiet cozy stay will definitely be staying there again "
United States
michael m.
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville
9.6 out of 10, Exceptional, (4)
"The location was handy and the property was exceptional. Beds were comfortable and the living room is a great space to gather for games, movies or relax with a book. The kitchen had everything we needed and there is ample dining space for larger groups, inside or on the deck. We made use of the fire pit and very clean grill and watched the fireflies at night. It’s very quiet, private and clean. Towels and linens provided were high quality. The host was very thoughtful and communicative. Our...
United States
Sonja H.
NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville
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."
United States
Monica R.
The price is AU$239
includes taxes & fees
25 Oct - 26 Oct
Quaint & Quiet 2 bed 1 bath
River Road Getaway
9.6 out of 10, Exceptional, (27)
"Property just as advertised nice place to stay. "
United States
Alison S.
The price is AU$370
includes taxes & fees
23 Nov - 24 Nov
River Road Getaway
Unique! A renovated old railroad depot turned into a cozy cottage.
10.0 out of 10, Exceptional, (122)
"Wonderful stay! Absolutely lovely property. We plan to come back in 2026!"
United States
Anna B.
Unique! A renovated old railroad depot turned into a cozy cottage.
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

Everything you need to know about Highland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Highland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland holiday rentals we have selected for you start as low as AU$201 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Highland?

Yes, there are holiday rentals close to the most popular sights in Highland, or you can select a more secluded option if you're looking for a relaxing stay. Highland is known for its parks.

What are some of the best holiday rentals that Highland has to offer?

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!: This holiday home rental outside of 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 that 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 wider area.

What’s a holiday rental in Highland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.