Vacation rentals in Darlington

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Top-rated vacation rentals in Darlington

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Top guest favorite
Tiny home in Darlington
4.98 out of 5 average rating, 52 reviews

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.

Top guest favorite
Home in Platteville
4.95 out of 5 average rating, 107 reviews

Pale Blue Dot

Live your best life at this colorful oasis. the Pale Blue Dot (aka Earth) that's here -- that's home -- that's us. The world is not just a place you live in, but a playground ready for you to conquer. Treat yourself, kids, pets, to nearby biking/walking trails, new Platteville Inclusive Playground or meander downtown to a quaint coffee shop. We welcome UW-Platteville sports enthusiasts, scholars, parents and friends. "The World is Yours" you ask? It's not just a catchphrase, it's a lifestyle.

Guest favorite
A charming log cabin is nestled among vibrant flowers and greenery. The structure features a large front porch with wooden railings and steps leading to the entrance. Tall trees surround the cabin, offering a natural and serene setting.
Home in Argyle
4.87 out of 5 average rating, 323 reviews

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.

Top guest favorite
Home in Darlington
4.97 out of 5 average rating, 71 reviews

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!

Top guest favorite
A friendly sheep stands in a green pasture, its fluffy wool coat visibly soft and light-colored. The sheep's gentle expression is captured as it gazes directly at the viewer, with trees and a cloudy sky in the background.
Farm stay in Argyle
4.98 out of 5 average rating, 337 reviews

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

Top guest favorite
The exterior of a one-story house is shown, featuring a light-colored façade and a neatly maintained yard. A gravel driveway leads to a two-car garage, positioned slightly to the right. The house is outlined by green grass and decorative landscaping.
Home in Darlington
5.0 out of 5 average rating, 7 reviews

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!

Guest favorite
Home in Mineral Point
4.92 out of 5 average rating, 13 reviews

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.

Guest favorite
A historic two-story house constructed with light-colored stone is showcased under a bright blue sky. The entryway features a wooden porch with seating, complemented by a neatly maintained grassy yard and surrounding trees.
Home in Darlington
4.94 out of 5 average rating, 109 reviews

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.

Top guest favorite
The farmhouse is shown from the exterior, showcasing a two-story structure with white siding and a covered front porch. Flower planters hang from the porch railing, and a stone pathway leads to the entrance. Green grass surrounds the house, bordered by a paved area.
Home in Gratiot
4.99 out of 5 average rating, 272 reviews

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.

Top guest favorite
The exterior of the revitalized car wash features a striking white facade with bold red accents. A vintage black truck is parked on the grass, while two bright red chairs sit invitingly near the entrance, adorned with a retro-style sign pointing towards the inn.
Home in Shullsburg
4.99 out of 5 average rating, 235 reviews

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

Top guest favorite
Home in Darlington
5.0 out of 5 average rating, 14 reviews

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.

Top guest favorite
A spacious living room is presented with decorative ceiling tiles and large windows offering views of Main Street. A dark sofa and an elegant chaise lounge complement the warm lighting from nearby lamps. Decorative curtains frame the windows, enhancing the room's character.
Apartment in Mineral Point
4.91 out of 5 average rating, 113 reviews

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

Popular amenities for Darlington vacation rentals