Vacation rentals in Randolph

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Top-rated vacation rentals in Randolph

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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, 394 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, 224 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
4.94 out of 5 average rating, 469 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!

Guest favorite
Cottage in Princeton
4.96 out of 5 average rating, 216 reviews

RiverFront Cottage>Private Pier>Firepit & Wildlife

Cute little cottage located right on the Fox River overlooking the peacefulness nature has to offer. Enjoy your very own private dock as well as 200 feet of river frontage surrounded by tall mature trees. Be submerged by the community of fishermen (& women) located on Puckaway Lake, surround yourself with wildlife, or paddle down the Fox River. Soak up the sun on the dock or learn how to build the best fire in the fire pit! The adventure is all around you! Which one will you be choosing?

Guest favorite
A cozy outdoor space features colorful pink chairs arranged around a fire pit, with a well-maintained lawn in front of a charming cabin. The cabin's large windows provide a view of the surrounding area, inviting relaxation under the open sky.
Cabin in Markesan
4.94 out of 5 average rating, 102 reviews

Lakefront 5 bed private pier, full rec lake w/air

Family-Friendly Lakefront Retreat on Little Green Lake - Your Perfect Getaway for Fishing, Kayaking, Boating, and Swimming! Full Rec Lake Life with Your Own Private Pier. Convenient Boat Launch less than a mile away. Short Drive by boat or car to Beach Access, Bar and Restaurant. Spa, and Golfing under 15-Minute Drive Away for Ultimate Relaxation and Fun! Boat rental available from Sunny Day boat rental. Rental not related to our cabin but they will bring a boat to the rental house dock.

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, 124 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
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, 104 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.

Guest favorite
A spacious bed with a white quilt and decorative throw is positioned against a deep green wall. Light is provided by side lamps atop nightstands. Three framed botanical prints enhance the ambiance, while large windows allow natural light to fill the room.
Apartment in Ripon
4.92 out of 5 average rating, 87 reviews

Downtown Loft with historic charm

Stay in historic downtown Ripon, less than a block away from it all! It has large beautiful windows to watch the downtown bustle, as well as see the magical night-time lights. The moment your leave the front door you'll have famous shops, on point drinks, amazing food, Wisconsin ice cream, retro candy, coffee shop, and much more! 10 minutes from Green Lake! 30 minutes from Oshkosh and Fond du Lac. Less than 90 minutes away from Appleton, Green Bay, Madison, Milwaukee, etc.

Guest favorite
The bungalow features a charming exterior with navy blue siding and a red door, flanked by well-maintained greenery. Two decorative oars are mounted on the wall, adding character, while a front porch offers a welcoming entrance. A driveway leads up to the home.
Bungalow in Green Lake
4.83 out of 5 average rating, 211 reviews

Peaceful Bungalow in Green Lake

Bright and airy bungalow located within short walking distance to downtown Green Lake, restaurants, boutiques, and boat rentals when in season. Located on beautiful Lake St, one block off the lake and with a partial lake view. The bungalow comes with 3 bedrooms, 1 bath, fully equipped galley kitchen, cable tv, and wifi. The huge screened-in porch is perfect for morning coffee and evening cocktails spring, summer and fall. Large sunny backyard. Come relax in beautiful Green Lake!

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, 161 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.

Guest favorite
The exterior of a two-story house is shown, featuring a porch and a well-maintained lawn. Large windows are visible, offering natural light to the interior. Surrounding trees provide shade, and a pathway leads to the entrance, enhancing accessibility.
Apartment in Oshkosh
4.86 out of 5 average rating, 243 reviews

No Cleaning Fees! 2 Bedroom Apartment By The Lake

We’re transparent with our pricing, that’s why we don’t have cleaning fees! The price you see is the price you pay (local taxes still apply). Come stay near the heart of Oshkosh - you’ll be on the second floor with views of Lake Winnebago. If you need anything during your stay we live on-site and are only a message away. Don’t worry though, the units are completely separated so you’ll have all the privacy you desire during your stay.

Popular amenities for Randolph vacation rentals

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  2. United States
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