Vacation rentals in Watertown

4.92 out of 5 average rating, 12 reviews

Two firepits are lit on either side of a quaint shed, surrounded by a grassy area. A calm lake reflects the soft glow of the flames, with trees providing shade and a tranquil backdrop. The evening sky displays subtle hues as day transitions to night.

Cabin in Hustisford

Unique Homes for a group getaway

Serenity Cottage and Firefly Cabin are two unique peaceful lake homes right next door to each other. Together these homes can sleep 12 comfortably and you will have access to three firepits, a small private island with two bridges, 2 kayaks, a pedal boat, 2 paddle boards, a pier, and a hammock. Enjoy fishing, exploring, relaxing views, and beautiful sunsets. A short walk gets you to a great restaurant/pub on the lake and a quick drive gets you to shops and bars. Only an hour from Milwaukee

4.96 out of 5 average rating, 54 reviews

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

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.

5.0 out of 5 average rating, 12 reviews

A welcoming seating area features two wooden chairs with gray cushions and a matching ottoman. A decorative round mirror is mounted on the wall above a wooden console table. Natural light filters through sheer curtains, enhancing the warm tones of the wooden accents.

Home in Lake Mills

Mid Century Modern Lake House!

Your home away from home! Leave your worries behind and enjoy a getaway at our Lakehouse! Our 3 bedroom, 1.5 bath a short walk to 2 amazing beaches! Enjoy a relaxing beach day at Bartle's or Sandy Beach, a bike ride on the Great Drumlin Trail, or sit around the firepit in our private fenced in backyard. Cook in a well stocked kitchen or snap the QR code for local take out. A spacious basement rec room with a laundry area, 65” TV, Air Hockey Table, foosball, and plenty of family friendly games.

4.92 out of 5 average rating, 198 reviews

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

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!

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.

4.94 out of 5 average rating, 203 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.

4.92 out of 5 average rating, 118 reviews

A charming home is set among lush greenery, showcasing large windows that allow plenty of natural light. A stone wall supports a decorative patio area with several outdoor chairs and potted plants, creating a serene outdoor space. Tall trees frame the scene.

Home in Nashotah

Beautiful home on Okauchee Lake, WI

I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

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.

4.9 out of 5 average rating, 91 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.

4.86 out of 5 average rating, 130 reviews

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

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.

4.95 out of 5 average rating, 197 reviews

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

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.

Vacation home in Oconomowoc

The exterior of the vacation home features a welcoming walkway leading to the entrance. A well-maintained lawn surrounds the house, and two white chairs are positioned on a small patio, offering a pleasant outdoor seating area. Lush greenery and landscaping enhance the setting.

Scenic 4 Bedroom WI Lake Home - Newly Renovated!

Located just 30 mins west of Milwaukee lies this fabulous vacation lake home featuring 4 bedrooms, 2 full baths and unbelievable views of the lake throughout the home. Many popular restaurants and bars nearby, including “The Hideaway” right next door. Full lake and pier access, great for fishing and swimming. Nearby boat rental also available. 2 queen, 2 twin, and 1 king size bed along with two couches. The home has been recently renovated and feels like new. Free parking available.

4.87 out of 5 average rating, 171 reviews

4.98 out of 5 average rating, 44 reviews

The exterior of the getaway features a charming log cabin style with multiple windows allowing natural light to fill the space. A landscaped yard displays a variety of plants and flowers, while nearby trees provide greenery. A barn-like structure can be seen in the background.

Home in Lake Mills

The Shack on Sandy Beach Road

A charming, cozy getaway centrally located in the quaint City of Lake Mills. The Shack on Sandy Beach Road features 3 bedrooms (king, queen and two twin beds), 2 full baths, and all the amenities to make your getaway complete. It is a 3 minute walk to crystal clear Rock Lake and Sandy Beach. Pickle Ball, playground, bowling alley, and ice cream shop are practically in the front yard. Enjoy a cup of coffee in the spacious backyard overlooking the Glacial Drumlin Bike/Walking Trail.

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.

5.0 out of 5 average rating, 36 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!

Popular amenities for Watertown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Watertown

4.98 out of 5 average rating, 43 reviews

The exterior of a charming farmhouse with classic white siding is surrounded by lush greenery and colorful flower beds. A covered porch extends along the front, featuring rocking chairs and decorative elements. Natural light enhances the welcoming atmosphere of this serene retreat.

Home in Rubicon

Farmhouse/ Erin Hills Golf Holy Hill Bowery Barn

4.97 out of 5 average rating, 60 reviews

Cottage in Johnson Creek

A-Frame Escape | Riverfront + Private Sauna

5.0 out of 5 average rating, 42 reviews

Home in Hartland

2-acre retreat steps from Nagawicka Lake

4.88 out of 5 average rating, 25 reviews

Home in Lake Mills

1 mile to Beach & Brewery. Walk downtown

Place to stay in Waterloo

The Loft at River's Edge

5.0 out of 5 average rating, 13 reviews

4.96 out of 5 average rating, 78 reviews

A serene bedroom features a spacious bed dressed in soft linens. Natural light filters through the window shades, illuminating the wooden floors and area rug. A wooden dresser and a chair are positioned nearby, contributing to the inviting atmosphere.

Farm stay in Burnett

Marsh Haven by Fieldview Estates

4.96 out of 5 average rating, 28 reviews

The exterior of the cottage features warm wooden siding and a welcoming porch with hanging flower baskets. A well-maintained pathway leads to the entrance, surrounded by lush greenery and low stone borders, creating a charming and inviting facade.

Home in Oconomowoc

The Paddle House