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Top Holiday Rentals in Highland

Highland: Driftless Fun Awaits

10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
The price is £184
includes taxes & fees
3 Sept - 4 Sept
Highland: Driftless Fun Awaits

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

10.0 out of 10, Exceptional, (477)
"We wanted to visit the Frank Lloyd Wright sites. Perfect location for all of them!"
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, (53)
"The four of us enjoyed staying at this home. We were really wowed by the beauty of the home, and the property was private and spacious. We had fun walking around enjoying nature. "
Elegant country retreat near Spring Green w expansive views of Driftless Region

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

10.0 out of 10, Exceptional, (148)
"Great cabin and solitude. Cabin is very nice and has everything. Really enjoyed the property."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

River Road Getaway

9.6 out of 10, Exceptional, (25)
"The set up of the property was very nice, multiple deck seating areas, very nice concrete fire pit right off the back deck. Park across the street, beautiful views of the scenic drive of the Wisconsin River, would really be beautiful to see in the fall with the leaves changing l."
The price is £179
includes taxes & fees
31 Aug - 1 Sept
River Road Getaway

A Comfy Cozy Cottage on Clowney

9.6 out of 10, Exceptional, (106)
"Was a wonderful place to stay"
The price is £158
includes taxes & fees
24 Aug - 25 Aug
A Comfy Cozy Cottage on Clowney

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

10.0 out of 10, Exceptional, (117)
"This is a cozy, delightful little spot in the middle of Wisconsin. We had a nice 3 day stay with no issues at all. The Depot was always nice and warm and welcoming. "
Unique! A renovated old railroad depot turned into a cozy cottage.

Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

10.0 out of 10, Exceptional, (33)
"We were delighted to be surrounded by nature and a comfortable and nicely equipped cottage."
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

Serenity cabin at Crooked Creek

10.0 out of 10, Exceptional, (8)
"Came up to see mom. Me and my siblings wanted something other that the typical 3 motel rooms. Cabin was clean and quiet. Nice to be able to share a weekend together without the spouses. Cannot wait to rebook for family reunion or another getaway. "
The price is £124
includes taxes & fees
26 Aug - 27 Aug
Serenity cabin at Crooked Creek

Suite in the heart of the center of spring green

9.8 out of 10, Exceptional, (83)
"Very nice and cozy, we will be renting again if available."
The price is £104
includes taxes & fees
1 Sept - 2 Sept
Suite in the heart of the center of spring green

Hotel Royal Apartment 2

2.0 star property
9.4 out of 10, Exceptional, (6)
"I love everything about the apartment"
Hotel Royal Apartment 2

Serenity Cottage at Mineral Point

10.0 out of 10, Exceptional, (89)
"What a wonderful place to stay. So much better than a hotel."
The price is £134
includes taxes & fees
24 Aug - 25 Aug
Serenity Cottage at Mineral Point

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

9.6 out of 10, Exceptional, (5)
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

Luxury Retreat in Prime Downtown Spring Green Location

10.0 out of 10, Exceptional, (54)
"Very clean comfortable and charming "
Luxury Retreat in Prime Downtown Spring Green Location

Downtown's Best View at Howdle's Retreat

10.0 out of 10, Exceptional, (3)
"Great to visit Mineral Point "
Downtown's Best View at Howdle's Retreat

150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI

9.6 out of 10, Exceptional, (85)
"We had the best time! We came for a little weekend getaway with the whole family and agreed that we'd all love to be back for a longer time. The House was everything we were looking for and absolutely lovely. It was the perfect fit all around. "
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI

Charming Crow Hill Cottage in welcoming Richland Center with BLOSSOMING garden

10.0 out of 10, Exceptional, (2)
"The home was so clean and welcoming, the cheese curds that we received were squeaky, and if you know anything about cheese curds, that means they are fresh! Had a great stay, we will be staying again when in the area."
Charming Crow Hill Cottage in welcoming Richland Center with BLOSSOMING garden

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

10.0 out of 10, Exceptional, (43)
"Was a wonderful Valentine’s Day weekend very quiet cozy stay will definitely be staying there again "
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin

Wildwood Retreat - Newly remodeled

9.4 out of 10, Exceptional, (6)
"It was perfect for us for the weekend!"
Wildwood Retreat - Newly remodeled

Amish-Built Cabin in the Driftless Area

10.0 out of 10, Exceptional, (66)
"Wonderful cabin. Had everything we needed plus everything we might of wanted. "
Amish-Built Cabin in the Driftless Area
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

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?

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.