Vacation rentals in Darlington

Chestnut Cottage

Built in 1890, Chestnut Cottage is located in the heart of the historic district within easy walking distance of shops, galleries, restaurants and historic sites. The Cottage features a comfortable living room, bright dining room, country kitchen, first floor bathroom and two upstairs bedrooms with one queen bed and one twin bed. Chestnut Cottage features artwork by prominent local artists. Wi-Fi, cable TV, DVD/CD players are included. Complimentary coffee/tea service. Minimum two night stay.

The Bower-Cozy Tiny home w/friendly farm animals

Escape to The Bower at Arbor Crest Acres, a peaceful woodland retreat designed with care and comfort in mind. Enjoy restful nights and unwind in a cozy, thoughtfully crafted space-perfect for slowing down and appreciating the serene beauty of Southwest Wisconsin’s countryside. As you explore, you will be greeted by our friendly animals: gentle Great Pyrenees on patrol, playful barn kitties, free-range chickens, adorable goat mamas and their babies, and shy ducks that seek refuge among the pines.

Relaxing 3 Bedroom Cabin with Hot Tub and Scenery

Tucked away in the rolling hills of Southern Wisconsin sits a little log home ready for your arrival. Hand built by the caretaker and his family; the Braezel Branch Retreat is named after the stream that runs through the valley. Relax with the whole family in this two-bedroom, two-bathroom cabin with a comfortable open floor plan. Wander through the beautiful walking trails and enjoy the view of the valley from the large front porch. There is also local tubing, kayaking, golfing and wineries.

FayetteGetaway: Hot Tub• Hiking• Lake• UTV Welcome

Come relax, play & explore at our 1/2-acre getaway. Just 6 minutes to Yellowstone Park! The Fayette ATV trail is a stone's throw away, with plenty of parking for trailers. Challenge your crew to our 6-hole Chipping Course, soak in the hot tub, gather around the fire, or enjoy outdoor games. Hungry? Walk to Rut Rohs-voted Wisconsin's #1 Dive Bar! Inside, you'll find a fully stocked kitchen, open living/dining space, 4 bedrooms, WiFi & board games. Come for the adventure, stay for the memories!

Rustic Barn Loft at Oak Springs Farm

Unplug in our gorgeous barn loft above our working barn. Sleep to the sound of crickets and frogs in the pond, then wake up and pet the sheep, goats, rabbits, cats, ducks & chickens. Open floor plan, cathedral ceiling, farm decor, fire pole, sliding barn doors. Full kitchen, jetted tub, rain shower, laundry. Stone patio, fire pit. 2 bedrooms, sleeper sofa, air mattresses. Juice, coffee, and fresh eggs provided when the hens are laying. NO A/C. ABSOLUTELY NO PETS Facebook oakspringsfarmwi

Darlington River View House - Direct Trail Access

Welcome to the Darlington River View House located in Darlington, WI near the exceptional River View Lodge Motel. From this property your view will include the beautiful Pecatonica River as well as the famous Cheese Country Trail. Also, located minutes from downtown Darlington, it is perfectly situated for whatever you choose to do while staying in the area. This house features 2 bedrooms, 1 bathroom, a two-car garage, and a fire pit with firewood provided. We look forward to having you!

Home away from home right off the trail

Discover the beauty of Southwest Wisconsin from this 2-bedroom country house located right off the Cheese County Trail located on trail accessible roads. This newly updated property features 2 queen beds and charging nightstands, 2 bathrooms, and a cozy living room with 2 futons. Along with a finished basement perfect for hanging out with a good game of euchre or kicking up your feet after a good day on the trail. In the peaceful spacious backyard, enjoy a night around the campfire.

Hamilton Goebel House

This house is a historic home that was built in 1833 on land owned by Jamison Hamilton, the founder of Darlington. It is not known if he actually lived in the house,but could be assumed. During your stay you will find bits of history and pictures that have been gathered along the way.It has all the comforts of home. A beautiful four bedroom home that has been completely renovated to reflect the old and new times. This home was on the list to be torn down by the city.

The Old Farmhouse

The old farmhouse is located on a quiet, dead-end road. It sits on top of a picturesque hill surrounded by rolling farmland. The Pecatonica river surrounds the farm on three sides. The farmhouse is the perfect place for quiet time and relaxation. The Farmhouse was built in 1914. It still has the original woodwork, and beautiful hardwood floors. Sit on the porch or sit around the fire pit and enjoy the beautiful fall foliage.

The Car Wash Inn A Unique Stay

Enjoy a unique stay inside a beautifully revitalized single bay 1950s car wash. Only minutes away from historic downtown Shullsburg. This space has been thoughtfully designed to retain it's industrial charm with a nostalgic ambiance, while offering modern amenities for a comfortable stay. ~20 miles to Galena, IL ~25 miles to Mineral Point, WI ~25 miles to Dubuque, IA ~ATV Trail Access with large parking area

The Windmill on Slough Rd

Bring friends and family to our peaceful, secluded house on Slough Rd. Large deck on the front and back of the house to enjoy the views and peaceful sunrise and sunsets. Outdoor fire pit to relax around at night. Very close to Cheese Country Trail for atv and utv enthusiasts, plus miles of road routes. 2 bedrooms and 1.5 bathrooms provide plenty of room for everyone. Full kitchen and laundry also available.

Main Street Mineral Point Hideaway WIFI - 3 Beds

Step into history at this 1861-built Mineral Point apartment on Main Street. Immerse yourself in the charm of small-town life. Witness summer parades and events from your living room windows. When you're set to explore, just head downstairs – you'll find yourself in the heart of downtown life. Your historical retreat awaits! Book your stay today! License #DWAT-CDB6MR