Holiday rentals in Watertown

4.96 out of 5 average rating, 25 reviews

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.

Guest suite in Sun Prairie

4.88 out of 5 average rating, 336 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.

4.92 out of 5 average rating, 170 reviews

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!

4.95 out of 5 average rating, 139 reviews

Cottage in Hartland

Cozy cottage in the heart of Lake Country

Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

4.97 out of 5 average rating, 249 reviews

Flat in Watertown

The Ernest Inn - Located downtown Watertown

Welcome to the perfect "home" away from home. This apartment is located in a historical building in the heart of downtown Watertown right on Main Street. This apartment features a complete kitchen, a working typewriter, a record player, a collection of classic vinyl, wifi, a smart tv, a brand new stone tile bathroom, and a back porch to relax and take in the sounds of downtown. This apartment is perfect for just one or two but can accommodate up to 6 guests. Licensed, insured, and inspected.

4.93 out of 5 average rating, 165 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.

4.9 out of 5 average rating, 59 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.

5 out of 5 average rating, 145 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Need 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 inspired getaway awaits!

4.96 out of 5 average rating, 191 reviews

Cabin in Fox Lake

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.

4.93 out of 5 average rating, 27 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.

4.95 out of 5 average rating, 339 reviews

Cabin in Whitewater

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.

5 out of 5 average rating, 63 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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Watertown holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Watertown

5 out of 5 average rating, 6 reviews

Home in Rubicon

Farmhouse/ Erin Hills Golf Holy Hill Bowery Barn

Jeffery ERating, 5 stars2 weeks ago

Eric was a great host. Let us check in early, and the place is better than it looks in the pictures! Can't get a more peaceful place to stay. Beds were great and house comes with everything you could ever need. I would stay again and recommend to anyone.

5 out of 5 average rating, 44 reviews

Apartment in Lake Mills

Lake Mills Retreat: 1 Mi to Beaches & Dining!

MichelleRating, 5 stars1 month ago

Very clean cozy place. Welcome wine and snacks. Seasonings and sugar, coffee pods nice touch.

4.97 out of 5 average rating, 186 reviews

Private room in Columbus

HA Whitney Inn, Columbus, Wisconsin

BeckaRating, 5 stars6 days ago

Great stay! The space was very clean. The little "extras" in the kitchen were a great surprise and very thoughtful. This space worked great for our short stay.

Tiny home in Lake Mills

4.8 out of 5 average rating, 20 reviews

The Yellow House

BrandeeRating, 5 stars2 weeks ago

Perfect location comfortable home away from home. Will stay there again.

Guest suite in Waterloo

4.77 out of 5 average rating, 31 reviews

Entire 2nd story of historic Farmhouse. Private.

SamanthaRating, 5 stars1 week ago

Amazing location and clean! Would stay again if needed

Private room in Fort Atkinson

4.96 out of 5 average rating, 109 reviews

The perfect getaway, quiet and safe! Single beds!

JohnRating, 5 stars1 week ago

Great place! Highly recommend. Would gladly stay here again when in the area.

5 out of 5 average rating, 17 reviews

Cottage in Beaver Dam

Sunset Bay Hideaway

KellyRating, 5 stars22 months ago

Our recent stay at this Airbnb was absolutely fantastic! From the moment we arrived, we were blown away by the cleanliness and attention to detail. Everything was tastefully decorated and it felt like a home away from home. It is evident that they genuinely care about their guests’s experience and comfort. Overall, this cottage had provided the perfect base of operations for our geocaching adventures in West Bend . I would not hesitate to recommend it to anyone looking to visit this area.