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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

10.0 out of 10, Exceptional, (436)
"Beautiful house and property, we enjoyed our stay here! The birdfeeder, fireplace and skylights were some of our favorites. The kitchen has everything you need - we utilized the grill and stove to make a few meals. The space worked well for 2 couples. I recommend this property if you’re looking for something in the area, and we would definitely choose to stay here again!"
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, (11)
"This was a perfect spot for our small family wedding. Our entire group loved this place. We were a little concerned if the traffic noise would be a problem, but we didn't even notice it. There were so many entertainment amenities, no one was without something to do during our stay."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Serenity Cottage at Mineral Point

10.0 out of 10, Exceptional, (74)
"Cozy home with good beds and kitchen"
The price is SAR 488
SAR 643 total
includes taxes & fees
30 Nov - 1 Dec
Serenity Cottage at Mineral Point

Enjoy peaceful surroundings

10.0 out of 10, Exceptional, (31)
"We had a wonderful stay at this lovely home, which was not only clean but also incredibly spacious, providing us with plenty of room to relax and unwind. The thoughtful details throughout the house made it feel welcoming and comfortable, and it was fully equipped with everything we could possibly need during our visit. The surroundings were absolutely picturesque, with beautiful scenery that enhanced our overall experience. We truly enjoyed exploring the area and appreciate the thoughtfulness...
Enjoy peaceful surroundings

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

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

10.0 out of 10, Exceptional, (27)
"Spring Green was a great halfway point for meeting up with friends. Three couples shared this beautiful house for a low key weekend. This unique property had everything we were looking for. The house is well-maintained, was fully stocked (especially the kitchen), and offers a spacious layout. The setting is beautiful. Barbara was a wonderful host."
Elegant country retreat near Spring Green w expansive views of Driftless Region

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)
"Hannah’s house was perfect for our stay. The beds were comfy, the living room just right for conversation and the outside view through the expansive glass windows so restful. We can hardly wait to revisit this sweet home! Thank you Hannah! "
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

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

The Hemlock/Hot Tub/Private Backyard/Golfing

9.8 out of 10, Exceptional, (9)
"Great location and wonderful home! Very convenient and comfortable!"
The price is SAR 845
SAR 1,224 total
includes taxes & fees
27 Nov - 28 Nov
The Hemlock/Hot Tub/Private Backyard/Golfing

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

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!

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, (4)
"Our extended family (6 adults and 5 kids) booked Brigham View so we could spend time together and visit House on the Rock. The spacious layout of the house accommodated our large group. We enjoyed making our own meals in the kitchen and we had plenty of seating for family style meals. The kids loved sharing the extra large bedroom and spread out over several beds. The two wings of the house allowed our two families to have some privacy, especially with separate bathrooms. The country setting...
Brigham View

Silver Birch Retreat. Spacious, pet friendly country home

9.8 out of 10, Exceptional, (6)
"A great time in rural Wisconsin! A very nice home near the quaint town of Livingston. All the amenities as if you were coming to your own home! Nicely decorated and plenty of space, cups, silverware, housewares, grilling necessities, seating and beds! The host was easy to work with and answered all questions in a timely manner! Overall worth every penny!"
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

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

10.0 out of 10, Exceptional, (436)
"Beautiful house and property, we enjoyed our stay here! The birdfeeder, fireplace and skylights were some of our favorites. The kitchen has everything you need - we utilized the grill and stove to make a few meals. The space worked well for 2 couples. I recommend this property if you’re looking for something in the area, and we would definitely choose to stay here again!"
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, (11)
"This was a perfect spot for our small family wedding. Our entire group loved this place. We were a little concerned if the traffic noise would be a problem, but we didn't even notice it. There were so many entertainment amenities, no one was without something to do during our stay."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Unique! A renovated old railroad depot turned into a cozy cottage.

10.0 out of 10, Exceptional, (106)
"We spent a week at the Depot while touring Wisconsin chasing the fall colours. We loved the decor of the cottage, the beds were comfortable & we enjoyed the country vibes. As the Depot is in quite an isolated position you need to consider bringing basic supplies with you. E.g milk etc. we only found out about the lack of onsite shopping when we arrived late at night. We found out where a supermarket was, once we arrived & read the information sheet. Richlands Center was a valuable resource...
Unique! A renovated old railroad depot turned into a cozy cottage.
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.