Highland Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 July - 23 July
Tomorrow
23 July - 24 July
This weekend
25 July - 27 July
Next weekend
1 Aug - 3 Aug

Holiday Rentals in Highland

Highland: Driftless Fun Awaits
Relax in this stylish living room with a plush sofa, coffee table, and floor lamps.

Highland: Driftless Fun Awaits

10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
The price is AU$323
includes taxes & fees
11 Aug - 12 Aug
Highland: Driftless Fun Awaits
Cheese Wedge Cabin Idyllic Farm
Relax on the covered porch with Adirondack chairs, surrounded by a deck and trees.

Cheese Wedge Cabin Idyllic Farm

The price is AU$515
includes taxes & fees
24 July - 25 July
Cheese Wedge Cabin Idyllic Farm
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Relax in this serene living area with a high ceiling, large window, and lush views of the surrounding greenery.

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

10.0 out of 10, Exceptional, (473)
"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
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
Relax in a cozy living area with a large sofa and coffee table, featuring a kitchen with modern appliances and a staircase to an upper level.

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

10.0 out of 10, Exceptional, (143)
"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
Elegant country retreat near Spring Green w expansive views of Driftless Region
Relax in a warm and inviting space with a high ceiling and comfortable seating area.

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

10.0 out of 10, Exceptional, (47)
"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
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
Relax on the deck with a comfortable seating area, dining table for two, and lush greenery surrounding you.

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

9.8 out of 10, Exceptional, (30)
"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
Enjoy cooking in this kitchen with a central island, stainless steel appliances, and ample cabinetry.

Hotel Royal Apartment 2

2.0 star property
9.4 out of 10, Exceptional, (6)
"Quiet and inviting. Close to shopping."
The price is AU$266
includes taxes & fees
23 July - 24 July
Hotel Royal Apartment 2
Unique! A renovated old railroad depot turned into a cozy cottage.
Relax in this inviting bedroom with a large bed, wooden headboard, and potted plants.

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

10.0 out of 10, Exceptional, (116)
"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.
A Comfy Cozy Cottage on Clowney
Relax in a serene outdoor space with a fire pit, wooden bench, and picnic table.

A Comfy Cozy Cottage on Clowney

9.8 out of 10, Exceptional, (103)
"Was a wonderful place to stay"
The price is AU$324
includes taxes & fees
3 Aug - 4 Aug
A Comfy Cozy Cottage on Clowney
Amish-Built Cabin in the Driftless Area
Kitchen features a central island, refrigerator, stove, microwave, and sink, with a window offering a view of the outdoors.

Amish-Built Cabin in the Driftless Area

10.0 out of 10, Exceptional, (65)
"Beautiful, secluded location. Everything about the cabin fit our needs as a larger group of six"
Amish-Built Cabin in the Driftless Area
Serenity cabin at Crooked Creek
Cozy cabin with a gabled roof and a small porch area, featuring a single window and a larger window on the upper level.

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 AU$269
includes taxes & fees
2 Aug - 3 Aug
Serenity cabin at Crooked Creek
NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville
Kitchen features a central island with bar stools, microwave, stove, sink, and refrigerator.

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

10.0 out of 10, Exceptional, (1)
"The location was handy and the property was exceptional. Beds were comfortable and the living room is a great space to gather for games, movies or relax with a book. The kitchen had everything we needed and there is ample dining space for larger groups, inside or on the deck. We made use of the fire pit and very clean grill and watched the fireflies at night. It’s very quiet, private and clean. Towels and linens provided were high quality. The host was very thoughtful and communicative. Our...
NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville
The Yellow Farm
Compact kitchen with stainless steel appliances, white cabinetry, and a tiled backsplash.

The Yellow Farm

9.6 out of 10, Exceptional, (17)
"Great place and location to stay close to house on the rock and cave of the mounds."
The Yellow Farm
The Guest House
Set amidst lush greenery, this traditional property offers a serene natural setting with a well-manicured lawn and garden areas.

The Guest House

10.0 out of 10, Exceptional, (27)
"Great property and location. Easy access and comfortable hospitality."
The Guest House
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
Swim surrounded by breathtaking views of the surrounding landscape from this pool area.

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

9.6 out of 10, Exceptional, (4)
"Lots of beds and endless amenities to keep our large group busy and having fun all weekend. Would definitely stay here again. "
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
Suite in the heart of the center of spring green
Kitchen area with central island, sink, and countertop, featuring wooden cabinets and a refrigerator.

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 AU$200
includes taxes & fees
5 Aug - 6 Aug
Suite in the heart of the center of spring green
River Road Getaway
Cozy cabin with a front door, small window, and star decoration, set amidst a wooden deck with a grill and seating area.

River Road Getaway

9.4 out of 10, Exceptional, (22)
"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 AU$369
includes taxes & fees
29 July - 30 July
River Road Getaway
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
Relax in a rustic, open-air setting with a central table and stools, surrounded by wooden crates and barrels.

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

9.6 out of 10, Exceptional, (82)
"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
Historic District, Charming Cottage, Sleeps 10
Enjoy a serene view of the lush outdoor area from the comfort of this room, featuring a large window and ceiling fan.

Historic District, Charming Cottage, Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$541
includes taxes & fees
28 July - 29 July
Historic District, Charming Cottage, Sleeps 10
Rustic Cabin at Crooked Creek
Surrounded by lush greenery, this cabin offers a peaceful retreat.

Rustic Cabin at Crooked Creek

9.6 out of 10, Exceptional, (5)
"Very lovely location. Quiet and clean. We will stay again (already our 2nd stay)"
The price is AU$239
includes taxes & fees
29 July - 30 July
Rustic 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Hotel Reviews

Best Western Dodgeville Inn & Suites

Best Western Dodgeville Inn & Suites

10/10 Excellent
"The hotel was extremely clean and well-kept. The service was fantastic, and the staff were friendly. I was so impressed with what a nice hotel this was at such a fair price!"
Kimberly 1-night trip
Posted 18 hours ago
Best Western Dodgeville Inn & Suites

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.