Highland Holiday Rentals

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Check prices for these dates

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Holiday Rentals in Highland

TV
Highland: Driftless Fun Awaits
Highland: Driftless Fun Awaits
10.0 out of 10, Exceptional, (1)
"Great property. Had everything we needed. Highly recommend. "
United States
Joshua
The price is HK$1,080
HK$1,985 total
includes taxes & fees
17 Nov - 18 Nov
Highland: Driftless Fun Awaits
TV, DVD player, books, video library
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
10.0 out of 10, Exceptional, (494)
"Exquisite cabin. This was our fourth stay and it is always very well maintained, providing a great place to get away and recharge. "
United States
JymAndLisa P.
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Smart TV, fireplace, DVD player, books
Elegant country retreat near Spring Green w expansive views of Driftless Region
Elegant country retreat near Spring Green w expansive views of Driftless Region
10.0 out of 10, Exceptional, (64)
"This house was lovely and very conveniently located to visit local attractions. "
United States
Lindsay R.
Elegant country retreat near Spring Green w expansive views of Driftless Region
Dining
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
9.6 out of 10, Exceptional, (22)
"Barn was beautiful, clean & fun amenities."
United States
Kerry S.
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Outdoor dining
Serenity Cottage at Mineral Point
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (98)
"What a wonderful place to stay. So much better than a hotel."
United States
Sharon L R.
The price is HK$1,049
HK$1,374 total
includes taxes & fees
26 Oct - 27 Oct
Serenity Cottage at Mineral Point
Indoor pool, a heated pool
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
9.6 out of 10, Exceptional, (5)
"Our stay was perfect. More than enough amenities and fine finishes. Kyle & Erin are very responsive and great hosts. Our stay could not have been better. "
United States
John M.
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
TV, fireplace, DVD player, books
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
10.0 out of 10, Exceptional, (157)
"Great cabin in a beautiful location! Both secluded and very comfortable."
United States
R J.
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
Outdoor dining
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
9.6 out of 10, Exceptional, (90)
"Lovely old farm house with lots of character in the beautiful Driftless area."
United States
Darlene M.
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
Interior
Suite in the heart of the center of spring green
Suite in the heart of the center of spring green
9.8 out of 10, Exceptional, (93)
"Wonderful place to stay! Clean, welcoming, comfortable--the perfect place to overnight when seeing plays at American Players Theatre."
United States
Jessica L.
The price is HK$594
HK$996 total
includes taxes & fees
26 Oct - 27 Oct
Suite in the heart of the center of spring green
Exterior
Serenity cabin at Crooked Creek
Serenity cabin at Crooked Creek
10.0 out of 10, Exceptional, (9)
"the place was peacefull and cozy, had everything we needed for our short stay, we enjoyed the outdoor fire pit a lot, seating outside in the porch with a morning coffee and enjoying the scenery was my highlight."
United States
Monica R.
The price is HK$738
HK$1,353 total
includes taxes & fees
19 Nov - 20 Nov
Serenity cabin at Crooked Creek
Outdoor dining
A Comfy Cozy Cottage on Clowney
A Comfy Cozy Cottage on Clowney
9.6 out of 10, Exceptional, (117)
"Comfortable, easy stay for a weekend. "
United States
Kelly
The price is HK$1,049
HK$1,615 total
includes taxes & fees
28 Oct - 29 Oct
A Comfy Cozy Cottage on Clowney
Fridge, microwave, coffee/tea maker, electric kettle
Luxury Retreat in Prime Downtown Spring Green Location
Luxury Retreat in Prime Downtown Spring Green Location
10.0 out of 10, Exceptional, (55)
"Host was very responsive and friendly and the location cannot be beat."
United States
Brian B.
Luxury Retreat in Prime Downtown Spring Green Location
Outdoor dining
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
9.8 out of 10, Exceptional, (41)
"We enjoyed fishing and the kayaks!"
United States
Teala B.
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
Fridge, microwave, oven, stovetop
Relax with beautiful views overlooking the Wisconsin River
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (52)
"The house was great, we had a very relaxing and fun vacation!"
United States
Wendy B.
The price is HK$2,315
HK$3,730 total
includes taxes & fees
24 Nov - 25 Nov
Relax with beautiful views overlooking the Wisconsin River
Outdoor dining
Spacious Cabin on the Wisconsin River!
Spacious Cabin on the Wisconsin River!
9.6 out of 10, Exceptional, (28)
"The property is beautiful and very comfortable. "
United States
Tina C.
Spacious Cabin on the Wisconsin River!
Fridge, microwave, oven, stovetop
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
9.8 out of 10, Exceptional, (48)
"Was a wonderful Valentine’s Day weekend very quiet cozy stay will definitely be staying there again "
United States
michael m.
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
Property grounds
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
9.6 out of 10, Exceptional, (4)
"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...
United States
Sonja H.
NEW Stunning views atop in the Driftless! 5 bedroom house on 4+ ac in Dodgeville
Private kitchen
Quaint & Quiet 2 bed 1 bath
Quaint & Quiet 2 bed 1 bath
10.0 out of 10, Exceptional, (1)
"the location was convinience for us considering my brother lives one block away.They were very nice to accommodate a very late check in."
United States
Monica R.
The price is HK$971
HK$1,189 total
includes taxes & fees
26 Oct - 27 Oct
Quaint & Quiet 2 bed 1 bath
Outdoor dining
River Road Getaway
River Road Getaway
9.6 out of 10, Exceptional, (27)
"Property just as advertised nice place to stay. "
United States
Alison S.
The price is HK$1,554
HK$1,853 total
includes taxes & fees
26 Oct - 27 Oct
River Road Getaway
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Unique! A renovated old railroad depot turned into a cozy cottage.
Unique! A renovated old railroad depot turned into a cozy cottage.
10.0 out of 10, Exceptional, (123)
"Wonderful stay! Absolutely lovely property. We plan to come back in 2026!"
United States
Anna B.
Unique! A renovated old railroad depot turned into a cozy cottage.
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

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

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

10/10 Excellent
"Lovely woodland getaway "
Cathy L. 2-night trip
Posted 2 days ago
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

Find out more about Highland

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

  • View our selection of featured holiday rentals in Highland
  • Use the map to find apartments and other holiday homes in the Highland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highland while they last

Look no further and take a look at our great range of rental properties in Highland!

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 Whispering Winds Winery 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.