Holiday rentals in Randolph

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Top-rated holiday rentals in Randolph

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A historic two-story home is showcased, featuring a light blue exterior and white trim. A welcoming porch is adorned with flower pots and includes a couple of white chairs. The driveway offers ample parking space, with a signpost displaying contact information.
Home in Princeton
4.93 out of 5 average rating, 225 reviews

Gray Gables Airbnb

Beautiful home built in 1904, newly remoldeled. Upstairs, 4 Bedrooms (Queen size beds)with full shared bathroom. Downstairs has living room, dining room /full kitchen. Half bath/laundry room. 2 Single beds downstairs on first floor, one is a trundle bed. 5 TV’s w/ Streaming Networks. WI_FI throughout. Huge porch w/ outdoor furnishings. Plenty of off road parking. Shopping and grocery store within walking distance. Base price for 1-4 people, after that $25.00 per guests, per night up total of 10.

Top guest favourite
Cabin in Portage
4.95 out of 5 average rating, 119 reviews

Secluded WI River Getaway w/ Hot Tub near Golfing

Get away from daily routines & refresh by the Wisconsin River at your private & peaceful retreat located near Devil's Lake, Cascade Ski & Devil's Head Ski/Golf Resorts & WI Dells. Perfect for families w/ 9 beds, 8 person Hot Tub, 6 Kayaks (May-Oct), Ping Pong, Foosball, Darts & Outdoor Games. The modern spacious design is filled w/ natural light, luxury comforts & new furnishings w/ Chef’s Kitchen, Weber Grill, Fireplace & Solo Stove. Ask us about nearby River Islands or day trips to ski/hike.

Top guest favourite
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
4.97 out of 5 average rating, 232 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.

Guest favourite
Cottage in Princeton
4.96 out of 5 average rating, 226 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 favourite
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, 104 reviews

5 bed lakefront with 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 favourite
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, 131 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.

Top guest favourite
Cabin in Princeton
4.97 out of 5 average rating, 236 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.

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 246 reviews

sauna and hot tub on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Top guest favourite
A scenic view showcases the modern home nestled among vibrant trees on a Christmas tree farm. Rolling hills are seen in the background, adorned with foliage in shades of red, orange, and green. Neatly arranged rows of Christmas trees line the foreground.
Home in Merrimac
4.99 out of 5 average rating, 135 reviews

Real Christmas Tree Farm! Skiing nearby

Get lost in nature and stay where the magic grows on a real Christmas tree farm! Situated on rolling hills below the Baraboo bluffs, this 125 acre farm and nature preserve has several miles of hike/bike/ski trails, a private lake and two creeks. Modern home in a quiet rural neighborhood. Easy drive on beautiful country roads to the many attractions in the area--less than 10 minutes to Devil's Lake State Park, Lake Wisconsin as well as Devil's Head & Cascade ski areas.

Top guest favourite
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, 155 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.

Top guest favourite
A cozy living area features light-colored sofas positioned around a coffee table, set against a backdrop of a large window overlooking greenery. A gas fireplace adds warmth, while a television is mounted above the mantel. Wood flooring enhances the inviting ambiance.
Home in Poynette
4.99 out of 5 average rating, 141 reviews

Spend your Summer at Beach Garden Bungalow!

Oooh, look! Here’s an awesome cottage right across the street from the Wisconsin River - Kayak heaven!! Relaxation and “re-creation” are what you’ll find here with plenty of fresh air, sunshine and river views. The home is located on nearly an acre of land with open yard space to stargaze by the fire pit as well as mature trees perfect for bird, deer, woodchuck and squirrel watching from the patio.

Guest favourite
The image captures a serene view of the Fox River, reflecting the surrounding trees and the clear blue sky. Sunlight filters through branches, creating a gentle glow over the water. The grassy bank provides a natural setting for relaxation or recreational activities.
Home in Montello
4.94 out of 5 average rating, 111 reviews

Grand Marsh Getaway

Grand Marsh Getaway is the perfect vacation destination for the entire family and offers something for everyone to enjoy. From the beautiful sunrise over the Fox River, great hunting, fishing, and wildlife, and direct water access to enjoy boating and leisure water activities. Please reach out with any questions specific to Grand Marsh Getaway or the Montello Area.

Popular amenities for Randolph holiday rentals

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