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Compare 36 Vacation Homes in Highland with updated reviews, rates, and availability.

Elegant country retreat near Spring Green w expansive views of Driftless Region
10.0 out of 10, Exceptional, (26)
"Evening night sky filled with view of the constellations and bright stars. Comfortable large outdoor spaces on multiple decks with plenty of seating and entertaining Incredible outdoor views can also be seen from indoor living space."
Elegant country retreat near Spring Green w expansive views of Driftless Region
River Road Getaway
9.6 out of 10, Exceptional, (11)
"Quick trip for my family reunion (right across from the park we had it at). Owner was very responsive to questions whether through VRBO or over the phone (returned my call super quick when needed help w/ TV). "
The price is AED 735
AED 884 total
includes taxes & fees
15 Nov - 16 Nov
River Road Getaway
Driiftless Cottage
9.8 out of 10, Exceptional, (27)
"Great bar restaurant one block away, friendly Staff. Everything you need convenience store down the street maybe a mile. Home was comfortable and felt safe"
Driiftless Cottage
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, (10)
"Kyle was an excellent host for our week long stay at the Barnhouse! He was very responsive to messages, and answered all our questions! It’s a great getaway, with plenty of space and an enough to keep people entertained! The view during our stay ( October) was amazing to wake up and watch the fall colors change o de the week we stayed! We definitely will stay again in the future! My wife was able to work over the WiFi for a few days in comfy cozy atmosphere , and the family enjoyed all...
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
10.0 out of 10, Exceptional, (435)
"Really enjoyed our stay. This cabin is lovely! The house feels incredibly cozy, but was also designed to be practical. The attention to detail in the decor really made this one of my favorite VRBO stays yet. "
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (39)
"Awesome stay. The property is beautiful. The house is very clean up to date. The four season porch room is awesome for morning coffee. Having a fire riverside was nice too. There is road noise as the house is close to the highway. But we will definitely stay again sometime."
Relax with beautiful views overlooking the Wisconsin River
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (74)
"Cozy home with good beds and kitchen"
The price is AED 477
AED 629 total
includes taxes & fees
15 Nov - 16 Nov
Serenity Cottage at Mineral Point
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River
10.0 out of 10, Exceptional, (97)
"The house was awesome! We had so much fun hanging out at the house. We enjoyed checking out cave of the mounds and then a birthday celebration for my 6 year old at the house. We fed the birds, took a walk, watched football, and drank plenty of apple cider. My sister from S.C. stayed with us and we enjoyed all the Frank loyd Wright books, area architecture. It was perfect!"
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River
MCM Influenced Home-*Sauna*
10.0 out of 10, Exceptional, (25)
"We had a great time staying in Spring Green for the weekend while visiting APT. It was great to be so close to the theatre in an awesome, clean home with great design! The dog loved having the fenced in yard to run around in too!"
MCM Influenced Home-*Sauna*
Private Ridge top Cabin/House
10.0 out of 10, Exceptional, (4)
"excellent experience with this property"
Private Ridge top Cabin/House
Pale Blue Dot
10.0 out of 10, Exceptional, (2)
"Went back home for a class reunion and enjoyed staying in this little home versus a hotel."
Pale Blue Dot
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
9.8 out of 10, Exceptional, (17)
"This was just right for a quiet weekend away. The dog loved the big yard too. "
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
Serenity awaits at this secluded riverfront property
10.0 out of 10, Exceptional, (43)
"3 of us stayed for 2 nights at this great house. For us it is all about the views and these were lovely. Very private and quiet. House had everything we needed and was cute, comfortable and very clean. Would stay there again."
Serenity awaits at this secluded riverfront property
Countainer House near Wisconsin River
9.8 out of 10, Exceptional, (86)
"You'd never guess you're staying in shipping containers! Very cute decor and extremely clean. This property is perfect for two couples with two identical bed/bath combos. It's very close to downtown Spring Green-quick and easy to get everywhere in the area. My husband and I walked along the DNR trails on the land right next to the property. Just a great place to stay!"
Countainer House near Wisconsin River
The Yellow Farm
9.4 out of 10, Exceptional, (13)
"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
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
9.8 out of 10, Exceptional, (74)
"Don’t plan on walking into town for shopping or lunch,etc. Driving to any destination is required. That issue was fine with our group. sitting on the deck with our morning coffee , or cocktail hour was great. Amazing antiques throughout the house "
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
The Limestone Lodge<br>A peaceful, rustic destination you won’t want to leave!
10.0 out of 10, Exceptional, (9)
"We spent a weekend at the Limestone for a Ladies Weekend. The house was beautiful, even better in person than the listing. The house fit the 11 of us comfortably and was very well equipped. Located very close to town. We enjoyed all the shops, Cafe 43, Crazy Frank’s, Brewery Pottery plus a hike around Pendarvis! Definitely recommend!! Please note that there are many stairs in the house which may be a consideration for some but not an issue for us (except after some wine). "
The Limestone Lodge<br>A peaceful, rustic destination you won’t want to leave!
Enjoy peaceful surroundings
9.8 out of 10, Exceptional, (30)
"4.5 stars. Patio door was hard to open. Place was overall clean. Would stay again"
Enjoy peaceful surroundings
Historic Wisconsin Retreat on 26-Acre Property!
9.0 out of 10, Wonderful, (4)
"Thank you for sharing your lovely home with us! Our family (three generations) made some wonderful memories in the pool, by the campfire, playing games, and hiking the beautiful trails. The property was absolutely beautiful all around and perfect for a peaceful family retreat in the countryside. Jamie was extremely responsive and helpful with anything we needed. We would highly recommend staying at this property!"
Historic Wisconsin Retreat on 26-Acre Property!
Brigham View
10.0 out of 10, Exceptional, (3)
"We were attending a wedding in Mt. Horeb, this home was close to the venue, provided ample space for the 6 of us. House was more than adequate for all of us, there are multiple restaurants in the area as well as a golf course 10 mins away which we enjoyed playing. Thank you & would consider staying there again in the future."
Brigham View
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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Other property types in Highland

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
10.0 out of 10, Exceptional, (435)
"Really enjoyed our stay. This cabin is lovely! The house feels incredibly cozy, but was also designed to be practical. The attention to detail in the decor really made this one of my favorite VRBO stays yet. "
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, (10)
"Kyle was an excellent host for our week long stay at the Barnhouse! He was very responsive to messages, and answered all our questions! It’s a great getaway, with plenty of space and an enough to keep people entertained! The view during our stay ( October) was amazing to wake up and watch the fall colors change o de the week we stayed! We definitely will stay again in the future! My wife was able to work over the WiFi for a few days in comfy cozy atmosphere , and the family enjoyed all...
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Elegant country retreat near Spring Green w expansive views of Driftless Region
10.0 out of 10, Exceptional, (26)
"Evening night sky filled with view of the constellations and bright stars. Comfortable large outdoor spaces on multiple decks with plenty of seating and entertaining Incredible outdoor views can also be seen from indoor living space."
Elegant country retreat near Spring Green w expansive views of Driftless Region
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.