Highland Holiday Rentals

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Holiday Rentals in Highland

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

10.0 out of 10, Exceptional, (436)
"Beautiful house and property, we enjoyed our stay here! The birdfeeder, fireplace and skylights were some of our favorites. The kitchen has everything you need - we utilized the grill and stove to make a few meals. The space worked well for 2 couples. I recommend this property if you’re looking for something in the area, and we would definitely choose to stay here again!"
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

10.0 out of 10, Exceptional, (11)
"This was a perfect spot for our small family wedding. Our entire group loved this place. We were a little concerned if the traffic noise would be a problem, but we didn't even notice it. There were so many entertainment amenities, no one was without something to do during our stay."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Unique! A renovated old railroad depot turned into a cozy cottage.

10.0 out of 10, Exceptional, (106)
"We spent a week at the Depot while touring Wisconsin chasing the fall colours. We loved the decor of the cottage, the beds were comfortable & we enjoyed the country vibes. As the Depot is in quite an isolated position you need to consider bringing basic supplies with you. E.g milk etc. we only found out about the lack of onsite shopping when we arrived late at night. We found out where a supermarket was, once we arrived & read the information sheet. Richlands Center was a valuable resource...
Unique! A renovated old railroad depot turned into a cozy cottage.

Serenity Cottage at Mineral Point

10.0 out of 10, Exceptional, (74)
"Cozy home with good beds and kitchen"
The price is AU$267
includes taxes & fees
8 Dec - 9 Dec
Serenity Cottage at Mineral Point

Enjoy peaceful surroundings

10.0 out of 10, Exceptional, (31)
"We had a wonderful stay at this lovely home, which was not only clean but also incredibly spacious, providing us with plenty of room to relax and unwind. The thoughtful details throughout the house made it feel welcoming and comfortable, and it was fully equipped with everything we could possibly need during our visit. The surroundings were absolutely picturesque, with beautiful scenery that enhanced our overall experience. We truly enjoyed exploring the area and appreciate the thoughtfulness...
Enjoy peaceful surroundings

Suite in the heart of the center of spring green

9.8 out of 10, Exceptional, (76)
"We were riding a motorcycle and visiting Spring Green. Great location, cute, clean and convenient. More restaurants open Wednesday thru Saturday "
Suite in the heart of the center of spring green

Relax with beautiful views overlooking the Wisconsin River

10.0 out of 10, Exceptional, (39)
"Awesome stay. The property is beautiful. The house is very clean up to date. The four season porch room is awesome for morning coffee. Having a fire riverside was nice too. There is road noise as the house is close to the highway. But we will definitely stay again sometime."
Relax with beautiful views overlooking the Wisconsin River

A Comfy Cozy Cottage on Clowney

9.8 out of 10, Exceptional, (87)
"Very comfortable stay. It gets a little warm in southwest bedroom, maybe some thicker curtains in that room"
The price is AU$352
includes taxes & fees
8 Dec - 9 Dec
A Comfy Cozy Cottage on Clowney

Amish-Built Cabin in the Driftless Area

10.0 out of 10, Exceptional, (56)
"We loved everything about this log cabin! It was spacious, clean, comfortable and wonderfully decorated. And we loved the location as well! Our host was very responsive to my questions and so helpful. We would recommend this cabin to anyone looking for a peaceful and quiet getaway. "
Amish-Built Cabin in the Driftless Area

Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

10.0 out of 10, Exceptional, (37)
"What it says on the tin—fixed up log cabin. Very decadent. Internet and TV was a bit spotty but better to stay off devices!"
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

10.0 out of 10, Exceptional, (131)
"The cabin is absolutely beautiful and you can't beat the land it sits on. Everything was immaculate upon arrival and we enjoyed our time there to relax and unwind. "
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

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

10.0 out of 10, Exceptional, (27)
"Spring Green was a great halfway point for meeting up with friends. Three couples shared this beautiful house for a low key weekend. This unique property had everything we were looking for. The house is well-maintained, was fully stocked (especially the kitchen), and offers a spacious layout. The setting is beautiful. Barbara was a wonderful host."
Elegant country retreat near Spring Green w expansive views of Driftless Region

The Guest House

10.0 out of 10, Exceptional, (24)
"Great property and location. Easy access and comfortable hospitality."
The Guest House

Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River

10.0 out of 10, Exceptional, (97)
"The house was awesome! We had so much fun hanging out at the house. We enjoyed checking out cave of the mounds and then a birthday celebration for my 6 year old at the house. We fed the birds, took a walk, watched football, and drank plenty of apple cider. My sister from S.C. stayed with us and we enjoyed all the Frank loyd Wright books, area architecture. It was perfect!"
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River

Private Ridge top Cabin/House

10.0 out of 10, Exceptional, (4)
"excellent experience with this property"
Private Ridge top Cabin/House

MCM Influenced Home-*Sauna*

10.0 out of 10, Exceptional, (25)
"Hannah’s house was perfect for our stay. The beds were comfy, the living room just right for conversation and the outside view through the expansive glass windows so restful. We can hardly wait to revisit this sweet home! Thank you Hannah! "
MCM Influenced Home-*Sauna*

Driiftless Cottage

9.8 out of 10, Exceptional, (27)
"Great bar restaurant one block away, friendly Staff. Everything you need convenience store down the street maybe a mile. Home was comfortable and felt safe"
Driiftless Cottage

The Hemlock/Hot Tub/Private Backyard/Golfing

9.8 out of 10, Exceptional, (9)
"Great location and wonderful home! Very convenient and comfortable!"
The price is AU$504
includes taxes & fees
27 Nov - 28 Nov
The Hemlock/Hot Tub/Private Backyard/Golfing

Pet-friendly Blue Mounds Vacation Rental w/ Yard!

3.0 star property
Pet-friendly Blue Mounds Vacation Rental w/ Yard!

Pale Blue Dot

10.0 out of 10, Exceptional, (2)
"Went back home for a class reunion and enjoyed staying in this little home versus a hotel."
Pale Blue Dot
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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Other types of properties in Highland you may be interested in

Don Q Inn

2.5 star property
8.0 out of 10, Very good, (920)
"Nice friendly staff. Breakfast was good and the room was clean."
The price is AU$93
includes taxes & fees
1 Dec - 2 Dec
Don Q Inn

Deer Valley Lodge & Golf

2.5 star property
8.8 out of 10, Excellent, (555)
"This place is comfortable, clean and has friendly staff, and the pool and hot tub are fantastic."
The price is AU$144
includes taxes & fees
27 Nov - 28 Nov
Deer Valley Lodge & Golf

Sleep Inn & Suites Lancaster-Platteville

2.5 star property
9.4 out of 10, Exceptional, (175)
"Our room was very quiet, no noise at all! Staff was friendly "
The price is AU$142
includes taxes & fees
12 Dec - 13 Dec
Sleep Inn & Suites Lancaster-Platteville
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin: This holiday home rental outside of Highland is located on a river, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What’s there to see and do in Highland?

Blackhawk Lake Recreation Area and Beach at Black Hawk 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.