Holiday houses in Jefferson

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Top-rated holiday rentals in Jefferson

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Top Guest favourite
A comfortable leather reclining chair is accompanied by a decorative pillow and a small round side table. A lamp stands next to the chair, and a cozy ottoman sits in front, enhancing the inviting reading nook beside a window dressed with navy curtains.
Apartment in Lake Mills
4.86 out of 5 average rating, 70 reviews

Super Cozy Apartment just steps from Downtown

Just steps from downtown! Enjoy shopping, dining, two breweries, a winery, and nightly live entertainment. LM has many community events happening throughout the year. This charming apartment is just 3 blocks from beautiful Rock Lake, and just minutes from the Glacial Drumlin Trail. Bring your bike, boat, or kayak, or rent one from a Local. Convertible sofa for third guest. Coffee and tea provided. * Exterior of property is still undergoing reno, we are working to bring it back to its glory.

Guest favourite
A branch adorned with delicate white flowers is positioned in a vase on a table, creating a soft focal point. In the background, a spacious bed is partially visible, with natural light entering from a window, enhancing the bright interior.
Loft in McFarland
4.97 out of 5 average rating, 213 reviews

#301 Private Apartment in Historic McFarland House

*** Our 2nd Floor is being remodeled throughout 2025 adding 4 more units to the old McFarland House This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1857 in the community that bears its name. Nestled in our small suburban downtown, this unit is perfect for travelers visiting the Madison area or nomads making a pit stop in the mid-west. Only 8mi to campus or a quick commute to the capitol, McFarland is an easy exit off multiple highways and interstates.

Top Guest favourite
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, 390 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 favourite
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, 193 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 favourite
An antique-style treasure map illustrates the Southeast coastline of Florida, featuring intricate details such as a ship image and a compass rose. The map's aged parchment texture and faded ink enhance its vintage charm, with marked locations and routes guiding potential treasure seekers.
Apartment in Fort Atkinson
4.99 out of 5 average rating, 170 reviews

“Goonies Never Say Die” You found theTreasure!

Enjoy the entire garden level of our home. Well appointed Queen Bedroom Suite. Generous kitchenette allows for snack prep. Home Gym coupled with a second queen suite. Living room w/Smart TV , Free Play Pac-man. Partially fenced yard and a 7 person Jacuzzi. Spa quality amenities in the private bathroom. During your visit none of the lower living area is shared with us or other guests. *We live on site and it’s possible you may have noise, like music, laughing or dog greetings during your stay.

Guest favourite
A charming two-story cottage features a gray exterior with textured siding and a gabled roof. A front porch is adorned with seasonal decorations, including pumpkins. Lush green grass surrounds the walkways, leading to the house's entrance. A few trees provide shade in the front yard.
Home in Lake Mills
5 out of 5 average rating, 5 reviews

The Yellow Door Guest House-Upper

Kick back and relax in this calm, cottage-space. We offer a unique UPPER UNIT in a turn of the century house that has everything you need to feel right at home. While staying in Lake Mills you can walk or bike downtown, enjoy the winery and breweries, and numerous specialty restaurants. Rock Lake is a few blocks from downtown. Explore the historical surrounding area such as the Glacial Drumlin Bike Trail, Aztalan State Park, and many seasonal events. We also offer the lower unit for guests!

Top Guest favourite
A wooden deck sits beside a serene lake, surrounded by lily pads. Two lounge chairs are positioned on the grass, offering a peaceful spot to relax. Nearby, trees provide natural shade, enhancing the tranquil outdoor setting.
Yurt in Cambridge
4.98 out of 5 average rating, 622 reviews

YurtCation

YurtCation is a relaxing getaway with lake frontage and nature trails. There is another yurt about 300ft up the same driveway. There are a total of two yurts and two homes that have access to the same 17 acre lake. Each yurt is off the grid and has their own queen-sized comfy bed, wood stove, Weber grill w/charcoal, fire pit, firewood, fresh water, canoe, and clean Porto Potty. Pet Policy: Max two - Must be in your sight and supervised at all times or $500 fine and check out immediately.

Top Guest favourite
Cabin in Fort Atkinson
4.91 out of 5 average rating, 153 reviews

Cozy Lake Cottage With The Best View & Pontoon!

Location, Location, Location! Incredible views! Retreat to this cozy Lake Koshkonong cottage with vaulted ceiling and southern exposure. Enjoy spectacular sunsets and views of the 10,000 acre lake from the north shore. Fish, hunt, boat, ski, swim, snowmobile, or simply soak up the sun and take in the view from this quiet retreat on a dead-end street. Fresh paint, bedding, and furniture make this little gem very comfortable. Great Walleye ice fishing right in front of this property!

Top Guest favourite
A spacious bed is adorned with textured decorative pillows in various patterns. The contrasting colors of the pillowcases complement the minimalist bedding. A sleek black lamp with a blue base is positioned on a nightstand, adding a pop of color to the serene sleeping area.
Apartment in Fort Atkinson
4.99 out of 5 average rating, 119 reviews

The Poet's Palace, an upscale, downtown flat.

This modern, yet eclectic apartment, has all the comforts of home. The decor is clean and chic, with just enough quirk! Located in downtown Fort Atkinson, some of the best restaurants, shops, and pubs are just outside your door or within a short stroll. Outdoor recreation opportunities are abundant, with the Glacial River Bike Trail, Fort River Walk, and numerous parks also within walking distance.Try your hand at fishing or launch a kayak from one of Fort Atkinson's public docks.

Top Guest favourite
The tranquil scene captures a vibrant sunset over the lake, reflecting hues of orange and gold on the water's surface. Silhouetted against the colorful sky, two ducks glide peacefully by the shoreline, framed by a quiet lake house and rocky beach area.
Home in Milton
4.99 out of 5 average rating, 121 reviews

Buoys UP! Lake Life & Sunsets

Looking to unwind & enjoy Lake Life-where weekends begin any day of the week-any season you choose? Here at Buoys UP! you will be able to do just that. Enjoy private access to our newly remodeled 2 bedroom lake house at Lake Koshkonong, WI. Overlook the private road this little gem is located on and enjoy the wonderful lake views and the beautiful sunsets. Stroll down the road for apx. a 2 minute walk to take advantage of your personal lake access Buoys UP! offers just for you.

Top Guest favourite
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, 157 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 favourite
The front view of a rustic stone cabin is framed by lush green trees. The structure features a wooden overhang supported by sturdy columns, with large windows allowing natural light to fill the interior. A neatly stacked pile of firewood is visible at the base.
Cabin in Whitewater
4.95 out of 5 average rating, 354 reviews

Glamping Cabin on Cold SpringTree Farm

Unfortunately we can't accommodate same day bookings as we don't have enough lead time to prep the cabin for your stay. Glamping on a working Christmas tree farm. Beautiful single room stone cabin with loft and wood burning stove. Two small beds in loft and futon on main floor folds out into full bed. Lots of room around to pitch tents as well. Situated on 40 acres of land with a pond, barn with basketball court, creek and Christmas tree fields.

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