Vacation rentals in Watertown

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Top-rated vacation rentals in Watertown

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Top guest favourite
A yurt is depicted, nestled among lush greenery. A wooden deck equipped with two chairs and an umbrella provides seating. The entrance features double doors framed by angled wooden roofing, with a wood-burning stove visible on the side. The surrounding forest offers a sense of seclusion.
Yurt in Cambridge
4.98 out of 5 average rating, 239 reviews

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Guest favourite
Home in Waukesha
4.93 out of 5 average rating, 190 reviews

Pet-Friendly Retreat•Sleeps 8•Huge Yard•Fire pit

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee on the private balcony. Evenings are perfect by the fire pit under a starry sky. Just a 5 minute drive from Pewaukee Lake Pet-friendly home with a large yard and fire pit - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.

Guest favourite
A two-story grey house with white trim is presented, featuring a welcoming front porch. The porch is furnished with four bright yellow chairs, providing a cheerful spot to relax. The entrance door is located on the left, and large windows brighten the facade.
Home in Oconomowoc
4.92 out of 5 average rating, 183 reviews

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Downtown Oconomowoc, beach, bandshell, bars, shops, restaurants, lakes, kayak/boat rental, 2 public golf courses in town and 3 more within 10 minute drive, 31 parks including the imagination station million dollar play area!!! Lots of local hiking and bike trails through the kettle moraine, visit Lapham peak, government hill, scuppernong, and much more! Minutes to Holy Hill, from the tower you can see the beautiful Lake Country area for miles. Only 1.25 hr drive to the Devils lake state park!

Top guest favourite
The cozy sitting area features a mix of patterned sofas and an armchair, with warm ambient lighting from two table lamps. Rich green walls create a comfortable environment, while a view into the dining area is visible through an open doorway, adding to the home's vintage charm.
Home in Watertown
4.93 out of 5 average rating, 191 reviews

Beautiful Victorian in Historic District

My Victorian home, "Belle Maison" (beautiful house), is waiting just for you. Newly restored, with 2 bedrooms, 2 baths - one with its original claw foot tub!- and a queen size sofa bed in the TV room. It is located in historic, downtown Watertown. Just a block from Main Street - with lots of shops and restaurants within walking distance - and the beautiful Rock River. The location is perfect - whether you're visiting Jefferson County or looking for a home base between Madison and Milwaukee.

Superhost
A two-story house features a blue exterior with large windows illuminated by natural light. Lush green shrubs flank the entrance, while a small seating area consisting of metal chairs is set on a well-maintained lawn. A concrete path leads to the front door.
Home in Oconomowoc
4.85 out of 5 average rating, 108 reviews

Oconomowoc Downtown River View

Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 242 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 spacious living area showcases a dark gray sectional sofa adorned with yellow and patterned cushions. A coffee table sits at the center on a patterned area rug, while a wall-mounted television is mounted nearby. Natural light enters through windows with a neutral-colored wall in the background.
Home in Delafield
4.95 out of 5 average rating, 196 reviews

Nagawicka Woods-Beautiful Lake Country Ranch Home

Welcome to Nagawicka Woods, a beautiful home located in Delafield, WI in the heart of Lake Country. Minutes from lake access to: Nagawicka, Okauchee, Pewaukee, Pine, Namahbin & Oconomowoc Lakes. 2 blocks from St. John's NW Military Academy, 6 minutes from Rogers Memorial Hospital, half an hour from Milwaukee & one hour from Madison. This home sleeps 6 (a pack n play is available.) Ideal for couples, family, small groups or a girlfriends getaway. Set on a quiet 1.5 private acres.

Top guest favourite
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, 390 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 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, 129 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, 167 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 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, 152 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 charming cottage is located near the water's edge, framed by lush green grass and a few trees. Outdoor equipment, including kayaks and a table setup for dining, adds convenience for guests. The exterior is painted in a soft blue, enhancing its inviting appearance.
Cottage in Hustisford
4.96 out of 5 average rating, 130 reviews

Charming and Cozy Cottage on Lake Sinissippi!

Pine Shore Retreat is a charming cottage so close to the lake that you feel like you are in a houseboat! The east side location means you have fabulous sunset views, as well as swimmable, hard bottom frontage off the platform pier. It is a small space, just one bedroom, but very cozy. Comfort is the focus, with new, high-end furnishings. The stainless steel refrigerator, granite countertops and a gas range in the kitchen offer a higher end experience.

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