Hillsboro Vacation Rentals

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Browse Select Hillsboro Vacation Homes

Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
10.0 out of 10, Exceptional, (18)
"Such a cute place and very clean. Thoroughly enjoyed sitting on the deck in the mornings and evenings and watching the wildlife. Will definitely be coming again. So many trails to hike and would love to kayak on the Kickapoo river nearby. "
The price is CA $161
CA $288 total
includes taxes & fees
Sep 30 - Oct 1
Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
Willow Creek Cottage
9.8 out of 10, Exceptional, (71)
"Already reserved for 2025 for our 4th stay here. Perfect spot. Love the senic area and all the small towns. Trout streams are great!"
Willow Creek Cottage
Small Cabin on West Fork Kickapoo River
9.4 out of 10, Exceptional, (12)
"My husband and I wanted a quiet getaway to end summer. This cabin fit the bill perfectly! We could relax and listen to the creek out back, watch wildlife and if the desire struck walk to the creek and fish. Will book again soon😁"
Small Cabin on West Fork Kickapoo River
Private vacation house for larger groups near the Dells with heated game room.
9.8 out of 10, Exceptional, (56)
"It was good "
Private vacation house for larger groups near the Dells with heated game room.
Dog-friendly log cabin on the river with deck & firepit - near Wisconsin Dells
8.6 out of 10, Excellent, (14)
"If you enjoy sharing your space with cockroaches and would love to bring them home with you then its great. Food and mouse poop in kitchen sink. Spiders, webs and mouse poop in whirlpool tub. Such a shame"
Dog-friendly log cabin on the river with deck & firepit - near Wisconsin Dells
5-mins from Viroqua-Cabin-Driftless Area-Near Lakes and Streams & Pet Friendly
10.0 out of 10, Exceptional, (51)
"House is exactly as shown and was nice. Location is good & easy to get to the town of Viroqua. Main floor bedroom is a bit tight. "
The price is CA $212
CA $442 total
includes taxes & fees
Sep 30 - Oct 1
5-mins from Viroqua-Cabin-Driftless Area-Near Lakes and Streams & Pet Friendly
Driftless Area Country House: large deck, spring fed creek, Amish area
10.0 out of 10, Exceptional, (69)
"Myself and my 6 sisters all get together every September for a long weekend getaway. Plenty of beds for everyone, nice and peaceful and enjoyed the area Amish farms."
Driftless Area Country House: large deck, spring fed creek, Amish area
Driftless-region sweet spot with a view right beside bike trail in Southwest WI!
9.8 out of 10, Exceptional, (18)
"Very clean, great location we were mostly "
Driftless-region sweet spot with a view right beside bike trail in Southwest WI!
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
9.6 out of 10, Exceptional, (16)
"This property was just beautiful we loved everything about it! The owner was very kind. I would highly recommend this place to anyone."
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
The Honey Haven
10.0 out of 10, Exceptional, (25)
"We enjoyed everything about The Honey Haven. Everything was perfec . One of our favorite things was being greeted by Boone. We fell in love w him immediately.Thank you so much. We would love to come back next year ."
The price is CA $215
CA $339 total
includes taxes & fees
Oct 8 - Oct 9
The Honey Haven
Upper Place Vacation Cottage
9.6 out of 10, Exceptional, (29)
"Lovely decorations. Well-stocked kitchen with everything we needed. Beautiful setting with spectacular star-filled skies. Would definitely come back."
Upper Place Vacation Cottage
This big old charming house Viroqua
10.0 out of 10, Exceptional, (14)
"Very comfortable house, everything we needed. Hosts were great!! "
The price is CA $270
CA $379 total
includes taxes & fees
Sep 30 - Oct 1
This big old charming house Viroqua
Hillsboro Guesthouse is remodeled & ready for you!
10.0 out of 10, Exceptional, (13)
"The cleanest and best maintained VRBO I have been in. Super host who provided lots of conveniences for all. Made our weekend stay for a family wedding awesome. Thank you Misti!"
Hillsboro Guesthouse is remodeled & ready for you!
Hilltop Home on 20 scenic acres. Close to Elroy -Sparta bike trails & much more
10.0 out of 10, Exceptional, (2)
"Everything went smoothly. Great property and Sandy was an excellent host!"
Hilltop Home on 20 scenic acres. Close to Elroy -Sparta bike trails & much more
Dogs Welcome! Lake House. Close to Dells!
9.2 out of 10, Wonderful, (7)
"Very peaceful and relaxing. Enough room for 10 people. Everything you need to have a gateway weekend or weekday."
Dogs Welcome! Lake House. Close to Dells!
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
9.0 out of 10, Wonderful, (71)
"We loved our stay here! The hosts were very friendly and helpful. The house was great for our family vacation. We really enjoyed the boats provided and hanging out on the deck and in the living room. We made use of the grill, too! The property has some short walking trails that were a fun activity too. Thanks so much!! "
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
Fischer’s Secret Cabin on Private lake
9.2 out of 10, Wonderful, (14)
"We had a bachelor party at Fischer’s cabin this weekend and everything exceeded our expectations. There are plenty of beds, bathrooms, and places to hang out. The basement is the ultimate space to have fun! There is also a lot of room outside for fun and the proximity to Castle Rock Lake is perfect. I will definitely be back here in the future."
Fischer’s Secret Cabin on Private lake
1909 Mansion in Reedsburg near Wisconsin Dells
9.8 out of 10, Exceptional, (8)
"While viewing several properties online, 11 year old granddaughter said, "Choose the mansion!" - wise choice. Our 3 generations family of 9 enjoyed gathering at the dinning room table that seated us all comfortably. The modern kitchen supported multiple preparers. Spaces to be together and spaces to be apart. Good location for lots of WI attractions."
1909 Mansion in Reedsburg near Wisconsin Dells
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (38)
"Lovely house and property!"
Relax with beautiful views overlooking the Wisconsin River
Secluded Rustic Cabin
9.8 out of 10, Exceptional, (37)
"The cabin was clean, comfortable and well stocked. The host was easy to contact and very helpful. The property is secluded and we saw tons of birds and lightning bugs. The hot tub was the perfect way to end the day after a long hike or a kayak trip down the Kickapoo river (Mr Ducks was a fantastic place to rent kayaks, tubes or canoes). Excellent dining and shopping in nearby La Crosse. Highly recommend!"
The price is CA $371
CA $635 total
includes taxes & fees
Sep 30 - Oct 1
Secluded Rustic Cabin
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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 Hillsboro

Blakley Hobbit Large Cabin
8.4 out of 10, Very good, (29)
"Except for what seemed like a lot of traffic for a country gravel road here in wisconsin, it was very peaceful. Night was quiet and comfortable. Had a nice fire outside and cabin was warm inside. Comfortable beds. Slight gas smell when we entered, but it seemed to dissipate once place was opened up. Attic type ladder to upper sleeping area was pretty shaky so I recommend using outside steps. Porta potties clean and fresh. An outside motion light would be nice for those who might need to venture...
The price is CA $121
CA $227 total
includes taxes & fees
Sep 27 - Sep 28
Blakley Hobbit Large Cabin
Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
10.0 out of 10, Exceptional, (18)
"Such a cute place and very clean. Thoroughly enjoyed sitting on the deck in the mornings and evenings and watching the wildlife. Will definitely be coming again. So many trails to hike and would love to kayak on the Kickapoo river nearby. "
The price is CA $161
CA $288 total
includes taxes & fees
Sep 30 - Oct 1
Eagle Valley Vista spacious, pet-friendly, close to parks, dark sky viewing
Rural Cabin in the Woods
9.2 out of 10, Wonderful, (33)
"We enjoyed our stay at this cabin! The location was awesome, a good place to unplug and relax away from the city. "
The price is CA $188
CA $292 total
includes taxes & fees
Oct 1 - Oct 2
Rural Cabin in the Woods
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.