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. "
Highland: Driftless Fun Awaits

Cheese Wedge Cabin Idyllic Farm

The price is NZ$553
includes taxes & fees
13 July - 14 July
Cheese Wedge Cabin Idyllic Farm

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

10.0 out of 10, Exceptional, (470)
"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, (46)
"Found our new place to stay when visiting family in the area. Would love to stay other times of the year. Thanks for everything! "
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, (143)
"The cabin was perfect for our family and friends! Definitely planning to come back!"
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area

Serenity cabin at Crooked Creek

10.0 out of 10, Exceptional, (6)
"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 NZ$273
includes taxes & fees
21 July - 22 July
Serenity cabin at Crooked Creek

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

10.0 out of 10, Exceptional, (114)
"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, (28)
"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

Hotel Royal Apartment 2

2.0 star property
9.0 out of 10, Wonderful, (4)
"Everything was great but the internet wasn't working for TV etc I should have contacted the host but dd t want to disturb him since it was kinds late"
The price is NZ$284
includes taxes & fees
11 Aug - 12 Aug
Hotel Royal Apartment 2

A Comfy Cozy Cottage on Clowney

9.8 out of 10, Exceptional, (101)
"Was a wonderful place to stay"
The price is NZ$348
includes taxes & fees
22 July - 23 July
A Comfy Cozy Cottage on Clowney

Amish-Built Cabin in the Driftless Area

10.0 out of 10, Exceptional, (61)
"Our host was very responsive. It was so peaceful and relaxing to be in nature. "
Amish-Built Cabin in the Driftless Area

NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville

NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville

The Guest House

10.0 out of 10, Exceptional, (27)
"Great property and location. Easy access and comfortable hospitality."
The Guest House

The Yellow Farm

9.4 out of 10, Exceptional, (16)
"We enjoyed our stay at the Farm House. It was clean and very comfortable to stay at. The location was perfect for us, attractions and restaurants within 20 minute drive."
The Yellow Farm

Suite in the heart of the center of spring green

9.8 out of 10, Exceptional, (81)
"Very nice and cozy, we will be renting again if available."
The price is NZ$214
includes taxes & fees
14 July - 15 July
Suite in the heart of the center of spring green

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

9.6 out of 10, Exceptional, (80)
"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

River Road Getaway

9.4 out of 10, Exceptional, (20)
"Good property & great location. Barb was a pleasure to work with & answered all my questions whether thru VRBO or over the phone. "
The price is NZ$397
includes taxes & fees
15 July - 16 July
River Road Getaway

Historic District, Charming Cottage, Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is NZ$575
includes taxes & fees
15 July - 16 July
Historic District, Charming Cottage, Sleeps 10

Rustic Cabin at Crooked Creek

9.6 out of 10, Exceptional, (5)
The price is NZ$257
includes taxes & fees
17 July - 18 July
Rustic Cabin at Crooked Creek

Relaxation cabin at Crooked Creek

9.0 out of 10, Wonderful, (2)
"Everything smooth and the cabin was very good "
The price is NZ$241
includes taxes & fees
14 July - 15 July
Relaxation cabin at Crooked Creek
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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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.