Vacation rentals in Waterloo

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Top-rated vacation rentals in Waterloo

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Guest favorite

A wooden staircase leads to the loft area, enhancing the home’s rustic charm. The open-concept kitchen features sleek countertops and wooden cabinetry, filled with natural light from large windows. A circular light fixture illuminates the dining area, which includes four black barstools at the counter.

Home in Lake Mills

4.95 out of 5 average rating, 208 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.

Guest favorite

A scenic view of a sunset reflecting vibrant colors in the sky over a tranquil waterway. Silhouetted trees create a natural frame along the shoreline, while gentle ripples on the water's surface capture the fading light of the day.

Guest suite in Sun Prairie

4.88 out of 5 average rating, 339 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.

Guest favorite

A fire table is positioned on a sleek surface, surrounded by a clear glass barrier that enhances the flame's glow. Two elegant glasses are set nearby, suggesting a cozy atmosphere for relaxation. A natural stone wall forms the backdrop, providing a serene outdoor setting.

Townhouse in Sun Prairie

4.95 out of 5 average rating, 150 reviews

1,650 sq ft, 3 bd, 2ba Ranch - All the comforts!

Centrally located just 15 minutes to the airport, 17 mins to downtown Madison, 45 minutes to Devil’s Lake, an hour to Milwaukee. Only a mile from dozens of restaurants, Costco, Target, and a Marcus Palace theater. Feel recharged when you sleep in the luxury hybrid beds. Be at home on the patio with a drink in hand while watching the fire table and cooking on the Weber gas grill. It work calls, no worries - plug into the docking station complete with keyboard, mouse and ultra wide monitor.

Top guest favorite

Apartment in Watertown

4.97 out of 5 average rating, 250 reviews

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.

Top guest favorite

The exterior of a Victorian home is shown, featuring a charming front porch supported by decorative columns. Lush greenery, including bushes and plants, surrounds the entrance, contributing to a welcoming appearance. Clear blue skies complement the crisp architectural details of the house.

Home in Watertown

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.

Guest favorite

Cabin in Fort Atkinson

4.89 out of 5 average rating, 118 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 favorite

Two goats are seen in a wooden crate filled with straw, one lounging comfortably while the other stands nearby. The goats are a mix of brown and white, showcasing their distinctive ears and features.

Tiny home in Darlington

4.98 out of 5 average rating, 757 reviews

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

Guest favorite

Home in Lake Mills

4.94 out of 5 average rating, 125 reviews

Rock Lake Retreat - Lake Mills Wisconsin

Welcome to the Rock Lake Guest House. Situated right on Rock Lake and only minutes away from charming "legendary" Lake Mills, this bright and light filled home gives you a stunning private wooded retreat with tree top views from every room. A cozy living room with charming built-ins and two patio doors to an expansive wrap around deck provides a scenic overlook to the lake. The house is a retreat for all seasons. Relax and unwind to this quiet, serene setting in an updated lake home.

Top guest favorite

An expansive garden area is seen, featuring several rectangular planting beds arranged in a grid pattern. A wooden table sits centrally, surrounded by vibrant greens and blooming flowers, with a backdrop of lush farmland extending into the horizon under a clear sky.

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 352 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!

Guest favorite

The entryway features a wall adorned with a decorative life preserver and a sleek flat-screen television mounted above a cozy fireplace. Pendant lights hang from the ceiling, providing warm illumination. A dining area with a wooden table and white chairs is visible, complemented by natural light from large windows.

Home in Edgerton

4.94 out of 5 average rating, 305 reviews

Vast Lake Koshkonong Views from Pier, Deck, & Home

Our 2 Bedroom, 1 Bathroom House is located directly on the shores of Lake Koshkongong. The back deck overlooks thousands of acres of lake with endless lake views. Just steps off the deck, one can enjoy the grassy landscape leading to the lakeside fire-pit. Then continue out onto the end of the 140 foot top notch pier. The pier (seasonally of course) includes a bench on the end and stairs into the water so that you can take a refreshing swim on our sandy bottom shoreline.

Top guest favorite

A modern coffee maker is positioned on a wooden countertop. The machine features a water reservoir on one side and a sleek black design with a single-serve brewing unit at the top. Glassware and kitchen utensils can be seen in the background.

Guest suite in Deerfield

4.95 out of 5 average rating, 130 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 favorite

A cozy outdoor fire pit area is illuminated by soft twinkling string lights. An Adirondack chair is positioned nearby, facing the glowing fire, surrounded by landscaped stones and plants, creating an inviting atmosphere for evening gatherings.

Cabin in Fox Lake

4.96 out of 5 average rating, 191 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.