Highland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 28 - Oct 29
Tomorrow
Oct 29 - Oct 30
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation 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 ￥21,248
￥39,045 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥22,700
￥29,646 total
includes taxes & fees
Oct 30 - Oct 31
Serenity Cottage at Mineral Point
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, (158)
"We were very happy with the amenities and the scenery "
United States
Dale M.
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
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!
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, (56)
"Host was very responsive and friendly and the location cannot be beat."
United States
Brian B.
Luxury Retreat in Prime Downtown Spring Green Location
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.
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, (10)
"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 ￥14,522
￥26,610 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥20,620
￥31,900 total
includes taxes & fees
Oct 29 - Oct 30
A Comfy Cozy Cottage on Clowney
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
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, (53)
"The house was great, we had a very relaxing and fun vacation!"
United States
Wendy B.
The price is ￥45,517
￥73,320 total
includes taxes & fees
Nov 24 - Nov 25
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)
"Great place for a large family! Very relaxing!"
United States
Anonymous traveler
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
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, (42)
"We enjoyed fishing and the kayaks!"
United States
Teala B.
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
Interior
River Road Retreat
River Road Retreat
9.6 out of 10, Exceptional, (18)
"Relaxing trip with family- lived the cabin and the kids loved the basement"
United States
Nora M.
The price is ￥30,548
￥36,740 total
includes taxes & fees
Nov 3 - Nov 4
River Road Retreat
Interior
Beautiful home located in the heart of Spring Green, close to area attractions
Beautiful home located in the heart of Spring Green, close to area attractions
10.0 out of 10, Exceptional, (22)
"Great location for the theater. Our host was very responsive and welcoming!! House is well furnished and very comfortable for a family group!! "
United States
Karlen
Beautiful home located in the heart of Spring Green, close to area attractions
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 ￥19,108
￥23,385 total
includes taxes & fees
Oct 30 - Oct 31
Quaint & Quiet 2 bed 1 bath
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.
View all properties
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

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 vacation rental in Highland?

Yes, we have vacation rentals near well known local attractions in Highland, or you can go with a more secluded option if you want a relaxing place to stay. Highland is known for its parks.

What are some of the best vacation home rentals that Highland has to offer?

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin: This vacation home rental near Highland is located on a river and has a patio, a barbecue grill, 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 vacation with amenities like 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 larger area.

What’s a vacation rental in Highland like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Highland. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.