Holiday houses in Watertown

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Top-rated holiday rentals in Watertown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Yurt in Cambridge
4.98 out of 5 average rating, 252 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

Top Guest favourite
Farm stay in Cambridge
4.99 out of 5 average rating, 103 reviews

Stay With Horses Escape Near Madison

Get ready for a quiet and peaceful stay. Take your pick: - 1King+1Queen Bed & 1 bath for 4 people - 1King+2Queen Beds & 2 baths for 6. (+$125 per night, contact host for payment) This home is attached to a barn with 6 Icelandic horses! Wake up to Icelandic horses just outside your window. A scenic escape with quiet mornings, fuzzy horses, and a one-of-a-kind IamGlytja experience - only 25 minutes from Madison - No horse riding allowed, owners to supervise all horse visits - No smoking / parties

Top Guest favourite
A cozy cottage is framed by vibrant autumn foliage, with golden and orange leaves carpeting the ground. The structure features large windows and a welcoming front door, while a small flower arrangement adds a pop of color. Tall trees create a serene and private setting.
Cottage in Watertown
4.98 out of 5 average rating, 49 reviews

Maple Cottage Retreat

Come discover the tranquility of our charming Maple Cottage Retreat. Nestled among tall mature trees, this spacious retreat offers ample room to breathe in the fresh, crisp country air and unwind in a setting that feels like a true haven. With tall mature trees surrounding the property, you'll have all the space you need to explore and take leisurely strolls. The interior exudes warmth and comfort. Adorned with tasteful decor, it strikes the perfect balance between modern convenience and charm.

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, 196 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.

Guest favourite
A single-story house features a light gray exterior with a sloped roof. The front yard is neatly maintained with green grass and several shrubs. A driveway leads to a garage on the left side, and large windows provide ample natural light to the living area.
Home in Watertown
4.9 out of 5 average rating, 90 reviews

Rock River Retreat

Bring your family to make memories enjoying a movie while sitting by the fireplace. Enjoy fishing during the day and a beautiful Rock River View. During winter you are right near the Jefferson County Snowmobile trails: and during the spring these trails are used for ATVs. There are several bike trails in town as well. If you are looking for things to do try the Octagon House or the local antique stores, outlet malls When you are ready to dine, Wisconsin is known for it's many supper clubs.

Guest favourite
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
4.87 out of 5 average rating, 120 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, 261 reviews

hot tub and sauna 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 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, 398 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
A blue cottage is framed by lush greenery and trees, featuring a stone patio with outdoor seating and an umbrella. Sunlight casts gentle shadows, highlighting the inviting entrance and landscaped surroundings.
Home in Watertown
5 out of 5 average rating, 31 reviews

Blue House in the Pines

Escape to your tranquil outdoor paradise! Cozy indoor & outdoor fires, hot tub in the trees, yard games, board games, chef's kitchen, book nooks, and more! No matter the season, you will relax and escape it all here. And if you are looking for action, there a ton of fun things to do in the area. Milwaukee and Madison are both 30 minutes away for day trips. We've got fishing, drive-in movie, skating rink, dinner theater, supper clubs, U-pick orchards, and even a golf farm!

Top Guest favourite
Cottage in Johnson Creek
4.97 out of 5 average rating, 37 reviews

A-Frame Escape | Riverfront, Fire Pit, Kayaks!

Escape to this cozy A-Frame on the Rock River with 100 ft of private frontage. Sip coffee at the bistro table, relax around the gas fire table, or wood fire pit. Inside, enjoy a loft bedroom, full kitchen, and modern comforts. Complimentary kayaks/canoe, pedal boat (upon request) invite you to explore the river. At the end of your day you can enjoy a seat in the sauna. Perfect for a peaceful retreat, yet close to Madison, Milwaukee, wineries, hiking, and much, much more!

Top Guest favourite
An open-concept kitchen showcases modern appliances, including a stainless steel refrigerator and a sleek range with an island. Two bar stools are positioned at the island, and a wall-mounted television is visible. Natural light fills the space through the window, highlighting the blue accent wall.
Home in Watertown
4.91 out of 5 average rating, 44 reviews

Modern Comfort in the Heart of Watertown

Charming farm house on the Rock River in Watertown, Wisconsin.  Old world architecture with modern kitchen and bathroom.  Living and dining room, two bedrooms and a loft, screened porches and a relaxing patio set up. This home away from home is designed to provide a stress free stay. Only two steps at the porch to enter, then all the spaces are easy access. No list of chores on your last day so you can enjoy your visit until the very last moments.

Guest favourite
A spacious living room features natural light flowing through large windows. A comfortable gray sofa is positioned alongside two armchairs, creating a cozy seating area. A light-colored area rug covers the hardwood floor, and a lamp provides additional illumination in the corner.
Home in Watertown
4.98 out of 5 average rating, 95 reviews

Watertown Family Retreat

The perfect peaceful place for families, couples, or individuals to relax during their stay. You will find places for a quiet cup of coffee in the morning, family meals together, and even toasting marshmallows for s'mores at the fire pit as the sun sets and the stars come out. Before turning in, maybe you might want to take a short ten-minute walk down to the bridge over the Rock River and see the moon reflected over the water.

Popular amenities for Watertown holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Jefferson County
  5. Watertown