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, (403)
"The cabin was great. Loved it all. Been a long time since we were in Wisconsin and forgot about mosquitoes but they were very welcoming. Really enjoyed our stay here"
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, (4)
"Our stay on the property was amazing. The house was lovely, had tons of natural light and wonderfully decorated. We loved walking the trail and going through the library. We stayed in mid-May & the weather was moody, thankfully there were fun puzzles and games to occupy those rainy portions of the day. There was plenty of space available for storing luggage. The mattress in the master bedroom was firmer that what we are used to but wasn't uncomfortable. The experience overall is quite memorable,...
Elegant country retreat near Spring Green w expansive views of Driftless Region
Close to Local Opera House - On the main drag
9.8 out of 10, Exceptional, (27)
"We loved the place & will come again. Loved the location & the town!"
Close to Local Opera House - On the main drag
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150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
9.8 out of 10, Exceptional, (59)
"Really cool property with amazing vintage details and antiques"
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
Unique! A renovated old railroad depot turned into a cozy cottage.
10.0 out of 10, Exceptional, (93)
"The house itself is so cool and unique- really beautiful! I also so much appreciate that the beds are comfy, nice quality sheets and pillows, and nice fluffy bath towels. Sometimes rental owners skimp on those- not here. Also had a little snafu with the house- nobody’s fault- and the owners were so kind and responsive to my needs. They are wonderful and attentive people and truly care that their guests have an amazing experience."
Unique! A renovated old railroad depot turned into a cozy cottage.
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, (4)
"Our family had a fantastic time! The host was flexible and generous, the accommodations beautiful, and the amenities unique and fun!"
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
10.0 out of 10, Exceptional, (118)
"A beautiful cabin on a beautiful piece of land. As described in the listing and absolutely peaceful. This is our second time staying here and we will be back."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
Enjoy peaceful surroundings
10.0 out of 10, Exceptional, (19)
"A wonderful way to spend time together. Close to activities shopping and restaurants but out in the country with pretty scenery and room to walk in the woods."
Enjoy peaceful surroundings
Suite in the heart of the center of spring green
9.8 out of 10, Exceptional, (57)
"This property is truly in the heart of spring green! The host was extremely responsive and sweet. We would absolutely stay there again."
The price is NZ$224
per night
2 Jun - 3 Jun
Suite in the heart of the center of spring green
Rustic, small and primitive cabin - Riverview Cabin, LLC
9.8 out of 10, Exceptional, (34)
"Sandy is a great host, checks in to make sure everything is good. Place is beautiful and perfect place to unwind. We will definitely be staying again! Thanks Sandy!"
Rustic, small and primitive cabin - Riverview Cabin, LLC
River Road Retreat
8.4 out of 10, Very good, (5)
"This was a beautiful new log house across the street from a spacious park and across the street from the Wisconsin River. It’d be a great staging spot for starting or ending a canoe/kayak trip on the river. The house is essentially new construction and made (entirely) of pine. The smell is fantastic. The check-in process was easy and the property manager made sure to let us know they were available if we had any needs. We enjoyed our stay. Just wish we could have adjusted our schedule to stay...
The price is NZ$395
per night
2 Jun - 3 Jun
River Road Retreat
Stunning Wisconsin Retreat on Active Farm!
10.0 out of 10, Exceptional, (12)
"Lots of fluffy pillows and towels, fenced dog yard is much larger than photos show and is adjacent to sport court so you can play tennis while the dogs play. Very friendly hosts even offered tractor rides. Organic crop farm with horses and goat in pen beside laneway. Very peaceful, plenty of space for dining or lounging. Lots of games, toys for the dogs, even dog dishes to use - thoughtful amenities for a comfortable stay. Not fussy modern, just comfortable and clean - perfect."
Stunning Wisconsin Retreat on Active Farm!
River's Edge Cabin, LLC
10.0 out of 10, Exceptional, (58)
"Great cabin on the river. Beautiful and peaceful play to stay!"
River's Edge Cabin, LLC
Beautiful home located in the heart of Spring Green, close to area attractions
Beautiful home located in the heart of Spring Green, close to area attractions
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (29)
"What a charming home! It was just as beautiful as the pictures, loved the view of the river, close to our daughter, loved cooking meals in the spacious kitchen & we loved ordering our food from The Port which was just up the road. The host (Holly) was very responsive and helpful. Hope to come back again!"
Relax with beautiful views overlooking the Wisconsin River
Amish-Built Cabin in the Driftless Area
10.0 out of 10, Exceptional, (47)
"Had a great time in SW Wisconsin!"
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, (17)
"We came to enjoy a weekend away from worries and we very much accomplished it! We enjoyed some local food and walked along the river in between playing games at the cabin. The cabin itself was very clean and cozy!"
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
Newly Renovated Cabin
9.4 out of 10, Exceptional, (21)
"The place is so beautiful and unique. The location was perfect for what we had planned. We spent a good amount of time at this location. The only complaints I have was the heat was not working. There were some minor things broken when we arrived. A drawer in the kitchen and one at the coffee bar buffet."
Newly Renovated Cabin
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (57)
"The property was comfortable, clean, and cozy. Bev was a thoughtful host."
The price is NZ$320
per night
1 Jun - 2 Jun
Serenity Cottage at Mineral Point
The Limestone Lodge<br>A peaceful, rustic destination you won’t want to leave!
10.0 out of 10, Exceptional, (3)
"Exceded my expectations. Want to plan a stay there again with a different group of friends. The Hosts were very accomadating. Mineral Point and the surrounding area is beautiful ."
The Limestone Lodge<br>A peaceful, rustic destination you won’t want to leave!
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See all available properties in Highland
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.

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, (809)
"Huge bath tubs and unique, fun, themed rooms make this an excellent stay. Breakfast is great too. We stay every time we're in the area. Definitely recommend this place if you are visiting the house on the rock!"
The price is NZ$138
per night
5 Jun - 6 Jun
Don Q Inn
Deer Valley Lodge & Golf
2.5 star property
8.8 out of 10, Excellent, (495)
"This was the last night in our 5 night trip and it was such a fun little place to end with! They have a water park, which is the main reason we picked it. Although it was during the week and our little was the only one on site, they were happy to turn on the extra water things for her. We enjoyed the water park and hot tub very much! Staff was very friendly and although the hotel is a little older, you can tell much pride and attention goes into keeping it nice!"
The price is NZ$198
per night
2 Jun - 3 Jun
Deer Valley Lodge & Golf
AmericInn by Wyndham Dodgeville
2.5 star property
8.0 out of 10, Very good, (385)
"Clean, comfortable room. Kids enjoyed the indoor pool and hot tub. Free breakfast was better than expected, with scrambled eggs, waffles, sausage links, biscuits and gravy, oatmeal, cereal, and toast/pastries on offer. Would stay again if in the area."
The price is NZ$222
per night
20 Jun - 21 Jun
AmericInn by Wyndham Dodgeville
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Highland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Highland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Highland. Seeing all the best attractions is bound to make you fall in love with Highland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Highland short-term rentals, that won’t be hard to do.

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.

Recent reviews of Highland properties
Expedia verified reviews