Holiday rentals in Watertown

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Top-rated holiday rentals in Watertown

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Guest favourite
The living room features two floral-patterned sofas arranged around a central coffee table. A wooden trunk provides additional storage. A large mirror reflects the light from a lamp atop a side table, while a guitar is displayed on the wall alongside potted plants.
Flat in Watertown
4.9 out of 5 average rating, 29 reviews

The Albert Inn - Located near Riverside Park

The Albert Inn is a conveniently located 2 bedroom upper apartment in the historic "Albert Kaddatz House". This apartment is one block away from Riverside Park, the tennis courts, the city swimming pool, and the Rock River in Watertown Wisconsin. It's also a short walk away from Watertown's historic downtown Main Street, many local restaurants, coffee shops, shopping opportunities, grocery stores, and is located 1.5 miles from Watertown Regional Medical Center. Licensed, insured, and inspected.

Guest favourite
Natural wood accents are featured throughout the entryway, highlighting a stone fireplace and a warmly lit chandelier. A decorative area rug provides contrast against the light wooden floor, while a cozy armchair invites relaxation near the staircase leading to the upper level.
Home in Lake Mills
4.95 out of 5 average rating, 225 reviews

The Treehouse

Welcome to the Treehouse. This is our home away from home—and hopefully yours too. We love coming to the treehouse just off clear Rock Lake. The Treehouse is a getaway, although there are neighbors, you feel as if you are nestled in a grove of trees. The house itself provides places where guests can linger, relax, sip a glass of wine or a cup of java or simply just be. One of my favorite features is the glass windows that wrap up around the ceiling so that it feels like the outside is coming in.

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, 41 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
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, 189 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

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
4.94 out of 5 average rating, 176 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
4.89 out of 5 average rating, 65 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.

Top guest favourite
Cabin in Fort Atkinson
4.91 out of 5 average rating, 144 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 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, 25 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
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
4.95 out of 5 average rating, 150 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
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, 209 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, swimming 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, including children. *All dogs/pets must be pre-approved by the host. There is a $50 pet fee/stay.

Top guest favourite
A charming bungalow is positioned near the edge of the Rock River. A well-maintained pathway leads up to the entrance, with vibrant greenery surrounding the area. The tranquil water reflects soft light, enhancing the serene setting.
Guest house in Horicon
5 out of 5 average rating, 26 reviews

Boathouse Bungalow

The Rock River Retreat Boathouse Bungalow is adjacent to the Rock River in the rural countryside of Dodge County, home of the treasured Horicon Marsh. Relax, refresh, and enjoy this magical place and the natural beauty that surrounds it. Discover and explore our undisturbed marshland by kayak, boat, or canoe. Spend time birding, biking, or hiking through this unique environment. Please join us for your time of connecting, discovery, and surprise.

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
4.92 out of 5 average rating, 39 reviews

Modern Comfort in the Heart of Watertown

SPRING FLASH PROMO: Book your stay by March 30 & Get a FREE Late Checkout! Relax a little longer – we’re rushing winter out, but you can stay! This exclusive offer ends soon. Book now for stay anytime in 2025 to grab this bonus. 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.

Popular amenities for Watertown holiday rentals

Quick stats about holiday rentals in Watertown

  • Total rentals

    10 properties

  • Nightly prices starting at

    € 34 before taxes and fees

  • Total number of reviews

    650 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

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