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

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Exterior
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
10.0 out of 10, Exceptional, (421)
"It feels like home away from home. "
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
Property grounds
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
9.8 out of 10, Exceptional, (14)
"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
Driiftless Cottage
Exterior
Driiftless Cottage
9.8 out of 10, Exceptional, (23)
"We had a wonderful trip to Montfort. This house was clean, charmingly decorated and comfortable. Instructions for checking in were clear, and the host was very responsive in helping me add an additional night to our stay. While it's a tiny town, the cottage was nicely situated near a public school and just down the street from a bar and grill with excellent burgers. "
Driiftless Cottage
Elegant country retreat near Spring Green w expansive views of Driftless Region
Exterior
Elegant country retreat near Spring Green w expansive views of Driftless Region
10.0 out of 10, Exceptional, (20)
"Unique and interesting home, totally in tune with the beautiful native surroundings. Peaceful and relaxing "
Elegant country retreat near Spring Green w expansive views of Driftless Region
Serenity Cottage at Mineral Point
Exterior
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (70)
"This property was perfect for our visit to Mineral Point. Would strongly recommend to others. "
The price is SAR 563
SAR 730 total
includes taxes & fees
28 Sep - 29 Sep
Serenity Cottage at Mineral Point
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River
Secluded Taliesin designed ranch on the 12th fairway of The Springs Golf Course.
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River
10.0 out of 10, Exceptional, (95)
"Watching the many different birds at the feeder, to the deer and their fawns in the fairway.. can’t find a much better stay for anyone who loves to golf!!"
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River
River Road Getaway
Exterior
River Road Getaway
9.8 out of 10, Exceptional, (8)
"My husband, three siblings and I stayed here for a family reunion which was in the park right across the street. It was a perfect location and the cottage was perfect for our visit to Muscoda. Highly recommend. "
The price is SAR 751
SAR 907 total
includes taxes & fees
30 Sep - 1 Oct
River Road Getaway
Countainer House near Wisconsin River
Living area
Countainer House near Wisconsin River
9.8 out of 10, Exceptional, (84)
"Enjoyed our stay very much "
Countainer House near Wisconsin River
Enjoy peaceful surroundings
Living area
Enjoy peaceful surroundings
10.0 out of 10, Exceptional, (27)
"Great house. Clean. Beautiful. We had wonderful time with friends… "
Enjoy peaceful surroundings
MCM Influenced Home-*Sauna*
Living area
MCM Influenced Home-*Sauna*
10.0 out of 10, Exceptional, (23)
"We loved the house. It is spacious, clean, and features a very well-stocked kitchen. The beds are very very comfortable! Our dog traveled with us and she absolutely loved the large fenced in backyard. A real plus was its location. We could walk to all of the shops and restaurants in downtown Spring Green. The host was very helpful and even allowed early check in. Thank you for a lovely stay."
MCM Influenced Home-*Sauna*
Private Ridge top Cabin/House
Living area
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
Interior
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
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Property grounds
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, (9)
"We loved getting together at the house! We are a farm family and loved what you’ve done with the barn! Our favorite spaces were the theater and the heated pool! Thank you for making it so easy! We would recommend the house to everyone with kids they had a blast!"
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Relax with beautiful views overlooking the Wisconsin River
Firepit overlooking the river
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (37)
"I can’t even begin to describe the amazing trip we had. The property itself is stunning and clean and just BEAUTIFUL! The backyard was expansive for the dogs to wonder. The fire pit was perfect for all day fires! When it got hot in the sun the wonderful living room was a great place to rest! "
Relax with beautiful views overlooking the Wisconsin River
Serenity awaits at this secluded riverfront property
Property grounds
Serenity awaits at this secluded riverfront property
10.0 out of 10, Exceptional, (41)
"Lovely property with great view of the river. Our favorite space was the screened in porch!"
Serenity awaits at this secluded riverfront property
The Yellow Farm
Terrace/patio
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
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
9.8 out of 10, Exceptional, (70)
"Wonderful time in a beautiful home, we enjoyed the house and the grounds!"
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!
Exterior
The Limestone Lodge<br>A peaceful, rustic destination you won’t want to leave!
10.0 out of 10, Exceptional, (7)
"We absolutely loved our stay at the Limestone Lodge! It was incredibly spacious! The decor is beautiful! During the day we enjoyed the breathtaking scenery of Mineral Point and the cute shops and eateries in the downtown area. In the evening we enjoyed using the karaoke machine and pool table. There was so much to do! The host is fabulous! Many amazing memories were made throughout our stay! Thank you Limestone Lodge!"
The Limestone Lodge<br>A peaceful, rustic destination you won’t want to leave!
Historic Wisconsin Retreat on 26-Acre Property!
Plain Vacation Rental | 4BR | 2BA | Stairs Required | 4,000 Sq Ft
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
Private kitchen
Brigham View
10.0 out of 10, Exceptional, (2)
"A great space big enough for larger families. Enjoy the beautiful views surrounding the property. Spacious and very clean. "
Brigham View
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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
Exterior
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
10.0 out of 10, Exceptional, (421)
"It feels like home away from home. "
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Elegant country retreat near Spring Green w expansive views of Driftless Region
Exterior
Elegant country retreat near Spring Green w expansive views of Driftless Region
10.0 out of 10, Exceptional, (20)
"Unique and interesting home, totally in tune with the beautiful native surroundings. Peaceful and relaxing "
Elegant country retreat near Spring Green w expansive views of Driftless Region
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Property grounds
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, (9)
"We loved getting together at the house! We are a farm family and loved what you’ve done with the barn! Our favorite spaces were the theater and the heated pool! Thank you for making it so easy! We would recommend the house to everyone with kids they had a blast!"
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
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.