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Vacation rentals in Randolph

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Top-rated vacation rentals in Randolph

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Superhost
Apartment in Portage
4.89 out of 5 average rating, 169 reviews

Comfy Nook, 5 Miles from Cascade Mountain

This apartment has two bedrooms and one bath. Located in downtown Portage, just 20 minutes from Wisconsin Dells easy access to the interstate. Cascade mountain just a few minutes away. There is a driveway for off-street parking for two cars. There is a private outside stairwell entrance and keypad door lock for access. This apartment is older construction and is on the 2nd floor. The floors are squeaky and noise will carry to the lower unit. Quiet time at 10:00pm. Just a short walk to downtown.

Top guest favorite
A two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.
Guest suite in Sun Prairie
4.89 out of 5 average rating, 400 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

Top guest favorite
A historic home features a multi-gabled roof and intricate architectural details. The exterior showcases a blend of light and dark hues, complemented by well-maintained landscaping and a spacious lawn. A charming porch wraps around the front, providing an inviting entrance with rocking chairs nestled on one side.
Home in Wales
4.94 out of 5 average rating, 195 reviews

Beautifully Restored Historic Victorian

Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

Top guest favorite
A red door with a decorative wreath opens to a outdoor patio area, featuring a comfortable seating arrangement and potted flowers. Lush greenery surrounds the space, enhancing the connection to nature, with a glimpse of the lake in the background.
Cabin in Fox Lake
4.96 out of 5 average rating, 225 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing and boating and in the winter have fun ice fishing on beautiful Fox Lake! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay. *Check out our “cottage on the trail”, closer to the lake.

Top guest favorite
A cozy log cabin is surrounded by a winter landscape, with a blanket of snow covering the ground. Several outdoor seating options, including a picnic table and benches, are visible amidst the snow. Firewood is stacked nearby, contributing to the inviting atmosphere.
Cabin in Adams
4.95 out of 5 average rating, 473 reviews

Cozy Log Cabin in the Woods

Adams County TRH License #7333 Welcome to the Lucky Dog Cabin! Nestled in the trees, our charming log cabin is located 25 minutes North of the Wisconsin Dells and less than 10 minutes from Castle Rock Lake, Wisconsin River, and Quincy Bluff State Park. Come relax, unplug, and get away from it all. Enjoy the fresh air, starry nights, and peaceful nature sounds. Our 9 acre property offers a beautiful trail that leads to gorgeous sunset views, through the forest. A true nature-lover's paradise!

Top guest favorite
The exterior of the barn features a sleek black facade with white trim, including multiple windows that allow natural light to enter. A wooden fence provides privacy, and the entrance is marked by a simple white door. Lush greenery surrounds the barn, enhancing its rustic charm.
Cabin in Princeton
4.99 out of 5 average rating, 126 reviews

Private Riverfront, Converted Barn *EV Charger*

Fox River Barn is located in a picturesque setting with stunning views of the Fox River in Princeton, WI. This 1940s barn has been lovingly converted into a comfortable living space with modern features and amenities, making it the perfect retreat for a romantic getaway or a peaceful escape from the city. Inside, the bones of the barn are present. From beams and rafters on the main level to the tall, gable barn ceiling. Just imagine all the different ways the barn had been used over time.

Guest favorite
The A-frame cabin is surrounded by mature pines, featuring a spacious lawn with a fire pit and several blue adirondack chairs. A charcoal grill is visible, and the deck includes umbrellas for shade, offering an inviting area for outdoor relaxation.
Cabin in Princeton
4.97 out of 5 average rating, 233 reviews

A-frame in the Pines

"Up North" cabin decor with modern amenities. Cute A-frame cabin nestled amongst mature red & white pines. Outside space to run & play or relax by the campfire or fireplace inside. Chargrill available. Bring your own charcoal. Living room with TV, dining area, kitchen & pantry, bathroom, & bedroom with a queen size bed on main level. The "loft" upstairs has 2 bedrooms, 1 with 2 twin beds , & the other space with a queen size bed and a reading area that opens up to your own private balcony.

Guest favorite
A serene lakeside view captures a vibrant sunset, with hues of orange and blue reflecting on the calm water. Clouds scatter across the sky, complementing the tranquil scene where the water mirrors the colorful sky, suggesting a peaceful natural environment.
Cottage in Poynette
4.86 out of 5 average rating, 105 reviews

Riverbluff Cottage *near WI's best hiking& Cascade

This cottage is located in a beautiful rural setting. Set back off the main street on a private dead-end gravel drive. It's quiet and dark. This is a simple, clean, and affordable space for those who are looking to get closer to nature. Conveniently located nearly equidistant to Madison, Wisconsin Dells, and Devil's Lake State Park. A wonderful HQ for exploring the natural beauty of Driftless Wisconsin. Plenty of hiking, skiing, wineries, and agri-tourism. This cabin is part of a duplex.

Top guest favorite
A cozy living area features a white-bricked fireplace with an arch-shaped mirror above it. A round table with two chairs stands adjacent to the fireplace, while a light blue chair is positioned nearby. Soft natural light enters through the window, enhancing the serene atmosphere.
Guesthouse in Sun Prairie
4.98 out of 5 average rating, 383 reviews

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

Top guest favorite
A cozy seating area showcases a wood-burning stove set against a rustic brick wall. A warm plaid blanket is draped over a plush sofa, while a small side table holds a book and a glass of wine. Soft light filters through large windows, highlighting the inviting atmosphere.
Cottage in Neshkoro
4.96 out of 5 average rating, 160 reviews

Pet Friendly Antique Schoolhouse with Fenced Yard

Pond Lily is truly a unique stay; a historic schoolhouse among tranquil surroundings. Beautiful traditional craftsmanship meets all the comforts of a modern home. Pet friendly with a fenced yard. A well-stocked kitchen makes for easy home-cooked meals. The layout is ideal for small groups looking to enjoy a peaceful getaway. Snuggle up by the wood-burning fireplace in the cold months or enjoy the firepit in the warm weather. For the outdoorsman, public lands are 5 minutes away.

Top guest favorite
The image depicts a charming three-building arrangement situated on a cul-de-sac. The structures feature varying architectural styles with a mix of siding colors. Lush greenery is visible in the surrounding landscape, and an American flag is displayed on one of the buildings under a blue sky with scattered clouds.
Guest suite in Deerfield
4.96 out of 5 average rating, 162 reviews

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Top guest favorite
The exterior of a two-story blue lakeside home is displayed, featuring large windows that allow for ample natural light. Adjoining the home, a well-maintained lawn is complemented by a fire pit area with light green Adirondack chairs, creating an inviting outdoor space.
Home in Beaver Dam
4.92 out of 5 average rating, 147 reviews

LakeLife is Dam Good! 4 Bedroom Waterfront Home

Fun for the whole family at this stylish lakeside home in the heart of Beaver Dam. The house as everything a group needs and wants for the perfect weekend, week, or overnight adventure. From the open floor plan living room to the exposed game room basement that leads right out to the lakeside yard. We've filled this home with all the touches needed to guarantee lake life living. The backyard overlooks thousands of acres of lake with endless lake views.

Popular amenities for Randolph vacation rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Dodge County
  5. Randolph