Destination Driftless- A Trailside Retreat

Photo gallery for Destination Driftless- A Trailside Retreat

A dining area with a wooden table, chairs, and a chandelier. There is a vase with flowers on the table.
A cozy living room with a leather sofa, a patterned ottoman, and a wooden door leading to another room.
A spacious living room with hardwood flooring, a wooden pillar, a black chair, and a small table with a candle.
A white two-story house with a sign reading "Destination Driftless" and a garage.
A grassy outdoor area with four Adirondack chairs arranged around a circular stone fire pit.

Reviews

9.2 out of 10
Wonderful

Highlights

  • Private garden
    A rare find — relax in the peaceful, private garden space.

Popular amenities

  • Patio
  • Barbecue
  • Air-conditioning
  • Pet-friendly
  • Refrigerator
  • Internet

Explore the area

View map
Darlington, WI
  • Place, Lamont Town Hall
    ‪12 min drive‬
  • Place, Yellowstone Lake State Park
    ‪22 min drive‬
  • Place, Apple River
    ‪25 min drive‬

Rooms & beds

3 bedrooms (sleeps 11)

sunrise

1 Queen Bed and 2 Single Beds

The den

1 Queen Bed and 1 Single Bunk Bed

Woodland retreat

1 Single Bed and 1 Queen Bed

2 bathrooms

Main level

Bathtub or shower · Bathtub · Toilet · Shower only

Upstairs bathroom

Bathtub or shower · Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden

Add dates for prices

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Exterior
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  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
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About the area

Darlington

Darlington is home to this holiday home. Badger Mine and Museum and Mineral Point Railroad Museum are local landmarks, and some of the area's activities can be experienced at Apple Canyon Lake Golf Course and American Wine Project. Roelli Cheese Haus and Monroe Arts Center are also worth visiting.
View more Holiday homes in DarlingtonOpens in a new window
Map
Darlington, WI

What's nearby

  • Lamont Town Hall - 12 min drive - 15.9 km
  • Roelli Cheese Haus - 19 min drive - 20.4 km
  • Yellowstone Lake State Park - 22 min drive - 26.7 km
  • Apple River - 25 min drive - 28.4 km
  • New Glarus Brewing Company - 40 min drive - 66.3 km

Getting around

  • Dane County Regional Airport (MSN) - 91 min drive

Restaurants

  • ‪Casey's General Store - ‬15 min drive
  • ‪Rocks Pour House - ‬13 min drive
  • ‪Glennie’s - ‬15 min drive
  • ‪Trail Birds - ‬14 min drive
  • ‪The Towne House - ‬14 min drive

Frequently asked questions

Is Destination Driftless- A Trailside Retreat pet-friendly?

Yes, this property allows cats and dogs (limit 2 total).

How much does it cost to stay at Destination Driftless- A Trailside Retreat ?

As of 30 October 2026, prices found for a 1-night stay for 2 adults at Destination Driftless- A Trailside Retreat on 10 April 2027 start from NZ$929, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Destination Driftless- A Trailside Retreat ?

On-site parking is available at the property.

What time is check-in at Destination Driftless- A Trailside Retreat ?

Check-in begins at 3:00 PM.

What time is check-out at Destination Driftless- A Trailside Retreat ?

Checkout is at 11:00 AM.

Where is Destination Driftless- A Trailside Retreat located?

Situated in Darlington, this holiday home is 9.9 mi (15.9 km) from Roelli Cheese Haus and 10.8 mi (17.4 km) from Yellowstone Conservation Area. Yellowstone Savanna State Natural Area and Cadiz Springs State Recreation Area are also within 16 miles (25 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 25 out of 37 reviews
Rating 8 - Good. 6 out of 37 reviews
Rating 6 - Okay. 6 out of 37 reviews
Rating 4 - Poor. 0 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

9.0/10

Cleanliness

10/10

Check-in

9.6/10

Communication

9.8/10

Location

9.2/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The surrounding property was beautiful and the house was very clean. There are many beds to select from and they are comfortable. If you're looking for a truly country experience, this house is perfect.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice location. Quiet and close to trails
Stayed 2 nights in Jun 2025
Verified review

6/10 Okay

Liked: Check-in, communication, location
Great location to the ATV trails but not enough room in the driveway for multiple trucks and trailers. The outside of the house needed to be power washed. Inside of the house was cute but the shower in the downstairs bathroom didn't work. The bedrooms had other rooms in them with beds. One bedroom had a bed in the closet and another had bunk beds then another room that had a slanted ceiling. There were three couples and this room was not fit for one couple. Every time the bedroom or upstairs bathroom door would open they woke up everyone in the house. There were tons of towels and toilet paper, etc. provided. Great place for a bunch of guys to stay but not for couples.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home with quick access to many fun things to do!

Perfect place to stay when visiting the Cheese trail, will definitely return to this property!
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was very nice and cleanI loved the decor. Location was great for riding side by sides.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved location

Wondering location not far from the ATV trails loved the old farm house feel and decor will definitely stay again hopefully longer next time !!
Stayed 2 nights in Aug 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay for riding Cheese County trail

Great location. Clean, easy to access. Fun weekend had by my group.
Stayed 2 nights in Aug 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great for 4 wheeling

The place is spacious inside and there are outdoor fire pits as well to be able to enjoy the outdoors.
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends SXS Trip

Great place to stay. We werent at the house much. Just to sleep and get ready. House decor is very cute.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beer Hogs UTV group

We have stayed here 2 previous times. We love the location. Thanks for sharing your home with us.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

UTV Ride

We have stayed here a few times. Everything is a thumbs up. We will be booking again. Thanks for share your place with us.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Country getaway

Nice home out in country. Peaceful and walk up street for great sunsets. 10-30 min to most towns or activities. Or just stay on property to escape.
Stayed 3 nights in Jul 2022
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rolling Green Hills

We stayed here to ride our ATVs on the Cheese Trail. The trail is a short two mile ride on a country road. We really enjoyed the rolling hills countryside. The bedrooms are all upstairs, which was a bit of a challenge, due to ongoing knee issues. We did enjoy our stay. Dustin was very responsive. Excellent Wifi. Cookies were great!
Rolling green hills!
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Old Farmhouse

Home is charming and cutely decorated. Comfortable beds, spacious bathrooms. We hosted a large family gathering. Weather didn’t allow for use of the nice outdoor space, but there was plenty of space inside for everyone to hang out in and visit comfortably for many hours. Large kitchen area perfect for serving meals to a crowd. Host was easy to reach and quick to respond. We will stay again!
Stayed 2 nights in May 2023
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location, listing accuracy
The beds were uncomfortable and one of the bedrooms was very cramped for one of the couples. Not enough space in the room. We did not use the bunk-beds. Did not like the idea it was pet-friendly.
Stayed 2 nights in Oct 2025
Verified review

6/10 Okay

Liked: Check-in, communication, location
Disliked: Listing accuracy

Nice hosts and location, house needs work

The hosts are very helpful and nice. The house has some nice features. The location is gorgeous However, we were not comfortable with the condition of the house--holes in the wall behind many outlets, old-fashioned wiring with electricity going from lightbulbs to power strips. I wouldn't bring toddlers again as there are too many decorative items within reach. If you do bring small children, bring your own plates, etc. for them as the beautiful dinnerware provided is not appropriate for kids. Also bring outdoor toys; there's a beautiful yard for kids.
Stayed 5 nights in Aug 2023
Response from VrboOwner on 3 September 2023
Anita, thanks for the feedback. It is a 100 year old home that has 100% updated wiring. However due to its old nature outlets are limited in a few of the bedrooms. In those rooms we do have some extension cord but the reminder of the house does not . As far as decorations go and nice dinnerware we do try to make it look nice and that might not fit a toddler. However we will get some plastic ware for future guest. Holes behind outlets I am not sure about. We do plan on having additional outlets wired to eliminate extension cords this winter during the slow season. We do thank you for your stay and feedback.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very Enjoyable Stay

Six of us stayed three nights in this roomy, comfortable farmhouse in the "middle of nowhere", that was delightfully quiet & serene. Except for the occasional milk-truck, with friendly drivers who waved, and a few ATV/UTV's, there is little traffic, especially after daytime hours.This is definitely farm country. All the bedrooms are on the 2nd floor, but we managed quite well ever though our ages run from 70 to 78. You just learn to be efficient with your trips upstairs. The sleeping arrangements were quite comfortable. The first floor living space was quite large with multiple rooms, comfortable seating & a large table for game-playing. The host was very responsive to questions and always quick to respond. I look forward to visiting this area again and wouldn't hesitate to stay here again.
Stayed 3 nights in Aug 2023
Verified review

6/10 Okay

Liked: Check-in, location
Disliked: Cleanliness

Filthy

Our family of 8 (Husband, myself and our 6 children ages 1 years old to 10 years old rented this home for 7 days 6 nights. My husband had a business trip so the family tagged along. We were so very thankful and impressed with the amount of space there was for sleeping and overall activity in the house. Unfortunately upon our arrival the house was filled with bugs inside the home. Loads were alive and some dead. We did our best to kill and cleanup the bugs to make our children feel safe and comfortable. While the bathrooms were pretty clean, the common areas were full of dust which isn’t helpful for one of our children who has asthma. The decor was simple yet nice. Unfortunately there was mouse poop in the kitchen drawer with all the utensils. While we are very understanding regarding mice being hard to handle at times, especially within the area the house is located (open fields). I would suggest the owners do their best to seal up the house better. And maybe hire a professional cleaning company between rentals. We loved the overall area surrounding the home. Great for scenic driving, which our family loves to do.
Stayed 6 nights in Dec 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, location, listing accuracy

Great stay

Great place to stay for visiting family in the area.
Stayed 3 nights in Nov 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Farmhouse

This property was close to the cheese trail and only six miles from downtown Darlington. We had an excellent time on the trail and enjoyed our stay!
Stayed 2 nights in Nov 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoyable Stay

We enjoyed our stay at the farmhouse with all of its character and charm. We had everything we needed and the beds were comfortable. We came to the area to hike some of the state parks and ride the ATV trails. The farmhouse is in a great location for accessing the Cheese Country Trail with the roads on both sides of the house (corner lot) being official ATV routes. Thanks so much for renting out your charming farmhouse!
Stayed 5 nights in Oct 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wisconsin Farm Vacation

We rented this property to give our Colorado kids a taste of the midwest and views of the beautiful landscape. It was well off the beaten path which is exactly what I was looking for. The photos definitely don't do the inside of the house justice. I loved the colors, style and repurposing of various items. I knew what to expect of some features that just come with older homes and I loved going from room to room and checking out all of the nice touches and surprises. There's plenty to do with indoor and outdoor games and activities and lots to do in the area. I was happy with the spices and pantry staples available. I would recommend bringing a few of your own knives if you love to cook. We picked up homemade bakery items and fresh produce from a farm stand nearby and cheese from Roelli cheese factory (fresh curd day on Friday!). All in all, we had a wonderful time and our hosts were friendly and quick to respond to messages. We would definitely stay here again.
Stayed 2 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

UTV trip with friends

This is the second time staying here. It is a great location for riding trails. We love it!!
Stayed 3 nights in May 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Short Stay for Platteville Graduation

A rustic farm house with tons of character. We did not have as much of a chance to enjoy the numerous outdoor amenities as we were in late and gone most of the following day. The scenery around the house is beautiful, many hills and curves, much different than other parts of Wisconsin. If you are looking to get away from the city this is the place go.
Stayed 2 nights in May 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property!

Lots of space, very clean, games and activities in the house and outside. I would highly recommend this rental and hope to come back again!
Stayed 2 nights in Oct 2021
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