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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. - Destination Driftless- A Trailside Retreat (Darlington)
Property grounds - Destination Driftless- A Trailside Retreat (Darlington)
A white two-story house with a sign reading "Destination Driftless" and a garage. - Destination Driftless- A Trailside Retreat (Darlington)
A cozy living room with a leather sofa, a patterned ottoman, and a wooden door leading to another room. - Destination Driftless- A Trailside Retreat (Darlington)
A spacious living room with hardwood flooring, a wooden pillar, a black chair, and a small table with a candle. - Destination Driftless- A Trailside Retreat (Darlington)
Nestled in SW Wisconsin's driftless region, this eclectic farmhouse offers a tranquil escape. From the front porch, watch Amish horse and buggy rides or catch sunsets over rolling hills. With full access to the house and outdoor space, enjoy grilling, hammocks, yard games like tree swings and fire pits.

Reviews

9.2 out of 10
Wonderful

Entire home

3 bedrooms2 bathroomsSleeps 11

Popular amenities

  • Kitchen
  • Pet friendly
  • Air conditioning
  • Outdoor Space
  • Parking available
  • Barbecue grill

Add dates for prices

About this property

Destination Driftless- A Trailside Retreat

  • Our eclectic farm house is nestled in the driftless region of SW Wisconsin! From the relaxing front porch you can occasionally watch the Amish strolling on horse and buggy, catch a great sunset over the rolling hills, or stargaze at night. We are located directly on the cheese county ATV/Snowmobile route so motor sports enthusiast can access this amenity directly off the driveway. Located within 20-35 min of several quaint tourist towns to include Galena , New Glarus, Monroe, Mineral Point,

    The space
    Guest have full access to the house. In addition we have a great outdoor space to include grilling, hammocks, yard games, tree swings, fire pits, outdoor projector for watching movies and making s’mores.

    Guest access
    Guest have full access to the house. In addition we have a great outdoor space to include grilling, hammocks, yard games, tree swings, fire pits, outdoor projector for watching movies and making s’mores.

    Other things to note

    Our home is a 100 year old farm house and runs on a septic system. Please only use the toilet paper provided (single ply) and please DO NOT flush anything other than waste and toilet paper down the toilet. This will cause a backup.

    NOTE:
    Please note that the front porch is a three season porch and may not hold a comfortable temperature during the cold winter months. Also note, that the three season porch baseboards should be kept on medium heat and not high, otherwise the breaker may pop.

    Another quirk with our old farmhouse are the main floor bathroom pipes. They have a tendency to freeze during extended periods of below freezing weather. This might make the main level bathroom unusable for winter stays. In order to prevent freezing ( if operational during winter stays ), please leave faucets in the main floor bathroom on a slow drip.

    Remembering these things will make your stay more enjoyable!

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub
  • Bathtub or shower
  • Shower
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Patio
  • Yard

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming cats and dogs only
  • 2 pets total

Suitability/Accessibility

  • Designated smoking areas

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden

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Policies

Check-in

Check-in time starts at 3:00 PM

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Please note garage is for personal use with the exception of garbage cans

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
2 total pets
Note from host: Per special request 100 dollar fee.

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings and birthday parties

Smoking

Smoking allowed: in designated areas

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings and birthday parties) are allowed on site; maximum attendees: 25
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the neighborhood

Darlington is home to this vacation home. Badger Mine and Museum and Nick Engelbert's Grandview are local landmarks, and some of the area's activities can be experienced at Yellowstone Golf Course and Apple Canyon Lake Golf Course. Roelli Cheese Haus and Mineral Point Railroad Museum are also worth visiting. Visit our Darlington travel guide
View more Vacation Homes in Darlington
Map
Darlington, WI

What's nearby

  • Large copper distillation columns in a building.
    New Glarus Brewing Company
    40 min drive - 66.3 km
  • 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
  • Yellowstone Golf Course
    25 min drive - 32.5 km

Getting around

  • Dane County Regional Airport (MSN)
    91 min drive

Restaurants

  • Casey's General Store
    15 min drive
  • The Spot Tavern
    14 min drive
  • Rocks Pour House
    13 min drive
  • Glennie’s
    15 min drive
  • China King
    13 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 is parking?

Onsite 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 ?

Check-out is at 11:00 AM.

Where is Destination Driftless- A Trailside Retreat located?

Situated in Darlington, this vacation home is 5.8 mi (9.3 km) from Lamont Town Hall and within 12 mi (20 km) of Roelli Cheese Haus and Yellowstone Conservation Area. Yellowstone Golf Course and Yellowstone Savanna State Natural Area are also within 16 mi (25 km).

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Destination Driftless- A Trailside Retreat Reviews

Reviews

Wonderful

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 22 out of 33 reviews
Rating 8 - Good. 6 out of 33 reviews
Rating 6 - Okay. 5 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

9.0

Cleanliness

9.6

Location

Reviews

Verified

10/10 Excellent

melissa t.

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

8/10 Good

Jason F.

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

10/10 Excellent

Christina R.

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

6/10 Okay

Danette M.

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

6/10 Okay

Anita D.

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
Verified

10/10 Excellent

Wayne G.

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

6/10 Okay

Gina D.

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

10/10 Excellent

Johanna D.

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

10/10 Excellent

Nikki W.

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

10/10 Excellent

Jeanne H.

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

10/10 Excellent

Srstenger@gmail.com G.

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

8/10 Good

Verified traveler

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

10/10 Excellent

Christina R.

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

8/10 Good

Judy I.

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

10/10 Excellent

Brian S.

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

10/10 Excellent

Suzanne W.

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

8/10 Good

Belle C.

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

10/10 Excellent

Mike C.

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

10/10 Excellent

Mary Jo O.

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

10/10 Excellent

Melissa F.

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

10/10 Excellent

Christina R.

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

10/10 Excellent

Bradley A.

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

10/10 Excellent

Jillian B.

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
Verified

8/10 Good

Marie W.

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

Friend Get a way.

The property gave us plenty of room and all that we needed. Hosts were great with checking in with us. Very relaxing!
Stayed 2 nights in Sep 2021
Verified

10/10 Excellent

Jean G.

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

Family gathering

4 out of state siblings celebrating our brother's, that lives in Darlington, 70 birthday. Beautiful house for a gathering. Weather was perfect, outdoor and indoor space were great for a gathering.
Stayed 3 nights in Aug 2021