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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 37 Vacation Homes in Highland with updated reviews, rates, and availability.

Elegant country retreat near Spring Green w expansive views of Driftless Region
Smart TV, DVD player, books

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

10.0 out of 10, Exceptional, (31)
"We had a fantastic time relaxing around the house and enjoying strolls through the prairie to the tea house to watch sunsets. This is a repeat visit for us and never disappoints. Thanks again."
Elegant country retreat near Spring Green w expansive views of Driftless Region
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
TV, DVD player, books, video library

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

10.0 out of 10, Exceptional, (446)
"We have stayed her several times and always have a hard time leaving. When we step inside any tension just drains away and we feel so at home. You can just spend hours watching all the birds on the large deck as you sit by the large fireplace. We love cooking in the open kitchen with the grill right outside the door on the back deck.Phyllis has supplied this clean cabin with everything you could need. "
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
Outdoor dining

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
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
Indoor pool, a heated pool

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

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
Outdoor dining

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

9.8 out of 10, Exceptional, (75)
"Four gals taking a weekend getaway found some peace and lots of laughter at this historic home. We loved exploring the home and all of the relics within it. The shed, the firepit and walking trail were lovely additions. We even saw a fox that lives nearby! Would definitely stay again. "
150 Year Old Home Situated in the Picturesque Rolling Hills of Southwest WI
Relax with beautiful views overlooking the Wisconsin River
Fridge, microwave, oven, stovetop

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
Silver Birch Retreat. Spacious, pet friendly country home
Property grounds

Silver Birch Retreat. Spacious, pet friendly country home

9.8 out of 10, Exceptional, (8)
"Great property in the middle of a farm field. We had 4 adults and 4 kids. Plenty of space. The fist thing the kids said was “this place is amazing!!” The kids room was indeed amazing - very large and a cool hang out for them. With bunk beds plus 3 other large beds. Large 8-person dining table we all fit at for eating and doing activities like cookie decorating, manicures, and painting/arts & crafts. The kitchen had everything. Such a cozy way to spend time playing games and watching...
Silver Birch Retreat. Spacious, pet friendly country home
The Yellow Farm
Fridge, microwave, oven, stovetop

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 awaits at this secluded riverfront property
Outdoor dining

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!
Exterior

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

10.0 out of 10, Exceptional, (98)
"We had a restful, wonderful time. Thank you. Everything we needed "
Escape to Serenity at The Covered Bridge Hideaway-The Perfect Vacation Rental!
Stunning Wisconsin Retreat on Active Farm!
Fridge, microwave, stovetop, dishwasher

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!
Private Ridge top Cabin/House
Miscellaneous

Private Ridge top Cabin/House

10.0 out of 10, Exceptional, (4)
"excellent experience with this property"
Private Ridge top Cabin/House
Picturesque Golf Course Home Near American Players Theatre, Taliesin & WI River
Outdoor dining

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
Dining

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

10.0 out of 10, Exceptional, (17)
"Barn was beautiful, clean & fun amenities."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Hot Tub/Golfing/King Bed @ The Hemlock
Fridge, microwave, oven, stovetop

Hot Tub/Golfing/King Bed @ The Hemlock

10.0 out of 10, Exceptional, (11)
"My siblings and I do an annual overnight. This place fit the bill. We will make it our annual location."
The price is AED 771
AED 1,131 total
includes taxes & fees
10 Mar - 11 Mar
Hot Tub/Golfing/King Bed @ The Hemlock
Beautiful home located in the heart of Spring Green, close to area attractions
Interior

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
Spacious Cabin on the Wisconsin River!
Outdoor dining

Spacious Cabin on the Wisconsin River!

9.6 out of 10, Exceptional, (25)
"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!
Charming Historic Getaway: Unwind in Lancaster's Timeless Elegance
Terrace/patio

Charming Historic Getaway: Unwind in Lancaster's Timeless Elegance

10.0 out of 10, Exceptional, (5)
"This property was amazing. The house was so homey and roomy. It was decorated so cute, and had plenty of space for everyone. It has an amazing seating area outside with a water fountain. We will definitely stay here again! "
Charming Historic Getaway: Unwind in Lancaster's Timeless Elegance
River Road Getaway
Outdoor dining

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 872 total
includes taxes & fees
7 Mar - 8 Mar
River Road Getaway
The Limestone Lodge<br>A peaceful, rustic destination you won’t want to leave!
Outdoor spa tub

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!
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

Cheese Wedge Cabin Idyllic Farm
Miscellaneous

Cheese Wedge Cabin Idyllic Farm

Cheese Wedge Cabin Idyllic Farm
Elegant country retreat near Spring Green w expansive views of Driftless Region
Smart TV, DVD player, books

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

10.0 out of 10, Exceptional, (31)
"We had a fantastic time relaxing around the house and enjoying strolls through the prairie to the tea house to watch sunsets. This is a repeat visit for us and never disappoints. Thanks again."
Elegant country retreat near Spring Green w expansive views of Driftless Region
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
TV, DVD player, books, video library

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

10.0 out of 10, Exceptional, (446)
"We have stayed her several times and always have a hard time leaving. When we step inside any tension just drains away and we feel so at home. You can just spend hours watching all the birds on the large deck as you sit by the large fireplace. We love cooking in the open kitchen with the grill right outside the door on the back deck.Phyllis has supplied this clean cabin with everything you could need. "
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.