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Compare 43 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, (35)
"The perfect place to relax and enjoy quiet beauty. The kids loved the puzzles, I enjoyed the sunset and the sounds of Barred Owls. We’ll be back. "
Elegant country retreat near Spring Green w expansive views of Driftless Region

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

10.0 out of 10, Exceptional, (455)
"Loved my stay at the Dyer's in Avoca. The calm and tranquility was just what I needed. My dog and I were quite happy there and look forward to a return visit."
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

9.8 out of 10, Exceptional, (19)
"The cabin was exactly what my husband and I were looking for. It was well appointed, clean, beautifully decorated, and located on a beautiful, serene lake. There was plenty of room for our two dogs to run and explore the property. We look forward to staying again!"
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly

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

10.0 out of 10, Exceptional, (11)
"The property felt like home as soon as we stepped through the front door. Fully appointed with everything one would need. Decor was very tasteful and warm. Our son loved the gym and the cool shower in the basement area. Highly recommend and should we be back in the area to visit family, we would definitely rent this beautiful property again!"
Beautiful home located in the heart of Spring Green, close to area attractions

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

Serenity Cottage at Mineral Point

10.0 out of 10, Exceptional, (82)
"What a wonderful place to stay. So much better than a hotel."
The price is AED 606
AED 787 total
includes taxes & fees
29 Apr - 30 Apr
Serenity Cottage at Mineral Point

Historic Stone House & Adjoining "Summer Kitchen" Bedrooms

9.8 out of 10, Exceptional, (10)
"Brisbane house was the perfect setting for my husband, myself, our 4 children and their partners plus 2 furry friends for our Christmas and New Years celebrations! Beautifully decorated for the holidays along with amazing artwork throughout the house. The layout of the house was perfect for us and the summer kitchen bedroom was bright and beautiful. Excellent communication from the host and beautiful walking/hiking trails throughout the property. Highly recommend!"
Historic Stone House & Adjoining "Summer Kitchen" Bedrooms

150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI

9.8 out of 10, Exceptional, (76)
"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

Hot Tub/Golfing/King Bed @ The Hemlock

10.0 out of 10, Exceptional, (13)
"A group of us were coming to the area to run a trail race at Governor Dodge State Park. Not many VRBO‘s will let you reserve for just one night, so we greatly appreciated this option, as it was Easter weekend and people needed to get home to their families by Sunday.The house was modern, clean and well appointed. It sleeps 12 and there were seven of us. Tons of room. The basement is cute as heck with its old time TV, rotary phone and foosball table. The bedrooms were comfortable and I...
The price is AED 1,446
AED 1,944 total
includes taxes & fees
28 Apr - 29 Apr
Hot Tub/Golfing/King Bed @ The Hemlock

Relax with beautiful views overlooking the Wisconsin River

10.0 out of 10, Exceptional, (40)
"This was the easiest stay I have had with a vacation rental. The house was beautiful, just like the photos, and stocked with anything you may need! Amazingexperience."
Relax with beautiful views overlooking the Wisconsin River

Serenity awaits at this secluded riverfront property

10.0 out of 10, Exceptional, (44)
"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

Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!

10.0 out of 10, Exceptional, (100)
"Our time spent at this property was ideal. It was very spacious for our large group. The views were picturesque as we sipped our coffee on the deck or were walking around the property. We especially enjoyed many hours of fun shooting pool! I would recommend this little piece of heaven to anyone looking to enjoy some time enjoying the piece and quiet of the country."
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!

Historic District, Charming Cottage, Sleeps 10

2.0 star property
The price is AED 716
AED 1,142 total
includes taxes & fees
29 Apr - 30 Apr
Historic District, Charming Cottage, Sleeps 10

Private Ridge top Cabin/House

10.0 out of 10, Exceptional, (4)
"excellent experience with this property"
Private Ridge top Cabin/House

Stunning Wisconsin Retreat on Active Farm!

10.0 out of 10, Exceptional, (18)
"Home was as described. Terrific location and no issues. Would highly recommend!"
Stunning Wisconsin Retreat on Active Farm!

Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River

10.0 out of 10, Exceptional, (98)
"This is a fantastic rental. The location site is absolutely beautiful backing up to the golf course fairway and is well maintained. The house is in great condition and the interior is even better than the pictures. It’s a short drive to the village of Spring Green and several great eating establishments. It’s also very close to Taliesin and House on the Rock. The owner is very good to work with and we had good communication. We thoroughly enjoyed this trip!"
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River

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

9.8 out of 10, Exceptional, (18)
"The property had enough space for our group of 12. The Party Shed was well used. The hot tub was a great size for the kids to have fun - deep enough for somersaults! The beds were comfortable. The workout room was used, the theatre room was great for "down time" - these 2 rooms were accessed through a bedroom. This house has mostly sliding barn doors (every interior door except for 1 bathroom) - so quietness and privacy was compromised. While it was great fun, there were maintenance items that...
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

10.0 out of 10, Exceptional, (2)
"Perfect spot for a family getaway"
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

River Road Getaway

9.4 out of 10, Exceptional, (14)
"The house was great for our 1 night. Open floor plan worked well for the kids and our lab. House was clean and in good repair, but bathroom could use some updating. Neighborhood was quiet and park and river were across the street. Would be nice for a summer stay also."
The price is AED 735
AED 876 total
includes taxes & fees
28 Apr - 29 Apr
River Road Getaway

Silver Birch Retreat. Spacious, pet friendly country home

9.8 out of 10, Exceptional, (9)
"Great place to stay! Very Clean and lots of room. "
Silver Birch Retreat. Spacious, pet friendly country home
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

Highland: Driftless Fun Awaits

The price is AED 397
AED 794 total
includes taxes & fees
30 Apr - 1 May
Highland: Driftless Fun Awaits

Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm

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

10.0 out of 10, Exceptional, (455)
"Loved my stay at the Dyer's in Avoca. The calm and tranquility was just what I needed. My dog and I were quite happy there and look forward to a return visit."
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
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.