Highland Holiday Rentals

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Holiday Rentals in Highland

Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
10.0 out of 10, Exceptional, 20 reviews
"This cabin was just what we needed for a final visit while our family finished our long distance move. The cabin was cute and was easy to get ahold of the owner when an issue popped up. They were so helpful and quick to respond 😊"
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
Unique! A renovated old railroad depot turned into a cozy cottage.
10.0 out of 10, Exceptional, 93 reviews
"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.
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
10.0 out of 10, Exceptional, 405 reviews
"This is an amazing property. Great location and great atmosphere"
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Close to Local Opera House - On the main drag
9.8 out of 10, Exceptional, 27 reviews
"We loved the place & will come again. Loved the location & the town!"
Close to Local Opera House - On the main drag
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, 59 reviews
"The cottage was surprisingly large and well-furnished. Location was perfect on a quiet side street."
The price is AU$297
includes taxes & fees
16 June - 17 June
Serenity Cottage at Mineral Point
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, 5 reviews
"So much fun! At times we had 22 people, yet never felt crowded. Had plenty to do even when it rained. They were quick to respond. Would stay here again"
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Amish-Built Cabin in the Driftless Area
10.0 out of 10, Exceptional, 47 reviews
"Had a great time in SW Wisconsin!"
Amish-Built Cabin in the Driftless Area
Enjoy peaceful surroundings
10.0 out of 10, Exceptional, 20 reviews
"This property did not disappoint. Every morning we met on the 2nd floor wrap around porch for coffee with binoculars and were dazzled by bird calls from warblers and vireo. During the days, we took short drives to Gov. Dodge, House, Tallesin, and the Wisconsin River towns. Every evening we gathered on the lower porch for a fire ring with drinks and dinner. Enough room on both levels for different activities including streaming entertainment and meditation. Groceries close by and some restaurants...
Enjoy peaceful surroundings
Stunning Wisconsin Retreat on Active Farm!
10.0 out of 10, Exceptional, 13 reviews
"Our stay was wonderful! The house had perfect accommodations for the 5 of us with room for several more! It contained ALL of the conveniences of home along with great water pressure in the showers, easy access to areas adventures, and very friendly hostess! Aside from a thoughtful welcome gift, she left us theee most beautiful and sweet tasting strawberries! LOVED THE EXPERIENCE and will definitely keep the reference for future stays in the area. "
Stunning Wisconsin Retreat on Active Farm!
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
10.0 out of 10, Exceptional, 118 reviews
"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
Elegant country retreat near Spring Green w expansive views of Driftless Region
10.0 out of 10, Exceptional, 6 reviews
"We had a great time staying at the country house. We enjoyed time on the deck, cooking in the kitchen, and walking the trails. It was a relaxing girls weekend!"
Elegant country retreat near Spring Green w expansive views of Driftless Region
Rustic, small and primitive cabin - Riverview Cabin, LLC
9.8 out of 10, Exceptional, 35 reviews
"Thanks"
Rustic, small and primitive cabin - Riverview Cabin, LLC
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, 30 reviews
"Home was nicely remodeled and clean. Even the 3 car garage was quite clean. Nice view of flowing river."
Relax with beautiful views overlooking the Wisconsin River
Riverside Chalet, LLC
10.0 out of 10, Exceptional, 33 reviews
"The Chalet was just beautiful with the view of the river and all the birds on the property. The cabin was cozy and welcoming with lovely antique furniture but all the modern conveniences. The hosts think of everything to make it a great stay."
Riverside Chalet, LLC
Luxury Retreat in Prime Downtown Spring Green Location
10.0 out of 10, Exceptional, 33 reviews
"Lovely accommodations, walked to restaurants and shopping. Would definitely stay here again. Host was communicative and easy to get ahold of."
Luxury Retreat in Prime Downtown Spring Green Location
The Guest House
10.0 out of 10, Exceptional, 21 reviews
"We found the property clean and perfect for our needs. The host was gracious and the loft was well supplied. They sell farm fresh beef and eggs. We had the eggs for breakfast each morning, what a treat. We would recommend Hollow Rule to anyone staying in the area."
The price is AU$209
includes taxes & fees
20 June - 21 June
The Guest House
Newly Renovated Cabin
9.4 out of 10, Exceptional, 21 reviews
"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
The Limestone Lodge<br>A peaceful, rustic destination you won’t want to leave!
10.0 out of 10, Exceptional, 3 reviews
"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!
Suite in the heart of the center of spring green
9.8 out of 10, Exceptional, 59 reviews
"Well appointed and charming apt in a great location. Everything that we needed. Shawn was responsive for minor questions. We can't wait to return. Highly recommend."
The price is AU$209
includes taxes & fees
30 June - 1 July
Suite in the heart of the center of spring green
River Road Retreat
8.4 out of 10, Very good, 5 reviews
"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 AU$367
includes taxes & fees
20 June - 21 June
River Road Retreat
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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

AmericInn by Wyndham Dodgeville
2.5 star property
8.0 out of 10, Very good, 388 reviews
"The property was clean and quiet, very nice pool area. Small breakfast "
The price is AU$192
includes taxes & fees
16 June - 17 June
AmericInn by Wyndham Dodgeville
Don Q Inn
2.5 star property
7.8 out of 10, Good, 815 reviews
"Large room, unique decor, nice pool area. Fantasuites options "
The price is AU$127
includes taxes & fees
17 June - 18 June
Don Q Inn
Deer Valley Lodge & Golf
2.5 star property
8.8 out of 10, Excellent, 502 reviews
"We really liked the individual nature of the Deer Valley Lodge - the decorating with antlers, the cabin-like furniture, it's a refreshing change from chain hotels. The room was clean, comfortable and the views from the hotel are just lovely. The breakfast is pretty minimal but we were glad to have it. And we liked the country location a lot."
The price is AU$173
includes taxes & fees
17 June - 18 June
Deer Valley Lodge & Golf
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.

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$209 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?

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
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