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Vacation Homes in Highland

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

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

10.0 out of 10, Exceptional, (46)
"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

10.0 out of 10, Exceptional, (29)
"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

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

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

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 AED 735
AED 884 total
includes taxes & fees
20 Jul - 21 Jul
River Road Getaway

Historic District, Charming Cottage, Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is AED 826
AED 1,276 total
includes taxes & fees
20 Jul - 21 Jul
Historic District, Charming Cottage, Sleeps 10

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

Downtown's Best View at Howdle's Retreat

10.0 out of 10, Exceptional, (3)
"Great to visit Mineral Point "
Downtown's Best View at Howdle's Retreat

Brigham View

10.0 out of 10, Exceptional, (9)
"Group of friends stayed for the weekend. Awesome house, beautiful views. Beds were very comfy!"
Brigham View

Entire 3 Bedroom House + Huge Wooded Yard

9.6 out of 10, Exceptional, (5)
"We had a very nice stay in Mineral Point! The house was clean and roomy for the 4 of us and when I had trouble with the VRBO app, the owner answered my call right away."
Entire 3 Bedroom House + Huge Wooded Yard

Beautiful home located in the heart of Spring Green, close to area attractions

10.0 out of 10, Exceptional, (15)
"Great place to stay in Spring Green! Really nice house"
Beautiful home located in the heart of Spring Green, close to area attractions

Pale Blue Dot

10.0 out of 10, Exceptional, (4)
"I wish I had found this property sooner. great location, wonderful house, great host that has good communication. "
Pale Blue Dot

Walnut Getaway Relaxing Country Getaway

10.0 out of 10, Exceptional, (7)
"Beautiful, peaceful setting! We loved everything about it! "
Walnut Getaway Relaxing Country Getaway

Stunning Wisconsin Retreat on Active Farm!

10.0 out of 10, Exceptional, (25)
"Home was as described. Terrific location and no issues. Would highly recommend!"
Stunning Wisconsin Retreat on Active Farm!

Serenity awaits at this secluded riverfront property

10.0 out of 10, Exceptional, (47)
"Loved how all the bedrooms were on the main floor! The porch is amazing."
Serenity awaits at this secluded riverfront property

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

9.8 out of 10, Exceptional, (20)
"Barn was beautiful, clean & fun amenities."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Relax with beautiful views overlooking the Wisconsin River

10.0 out of 10, Exceptional, (45)
"Lovely house and property!"
Relax with beautiful views overlooking the Wisconsin River

Historic Stone House & Adjoining "Summer Kitchen" Bedrooms

10.0 out of 10, Exceptional, (11)
"Host and house were great. Large secluded peaceful and historic property. Enjoyed our stay."
Historic Stone House & Adjoining "Summer Kitchen" Bedrooms

Spacious Cabin on the Wisconsin River!

9.6 out of 10, Exceptional, (26)
"We had all the room we needed and more for our family time at this rental. Lovely views of the river and a great outdoor space. Would recommend for a larger family/group for sure. "
Spacious Cabin on the Wisconsin River!
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