Vacation rentals in Waterloo

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Top-rated vacation rentals in Waterloo

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Guest favorite

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, 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 two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.

Guest suite in Sun Prairie

4.88 out of 5 average rating, 345 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 spacious living area features a large brown leather sectional sofa, accented with decorative pillows. A glass-top coffee table sits on a plush rug. In the background, a dining area with a modern table and light fixture is visible.

Townhouse in Sun Prairie

4.95 out of 5 average rating, 153 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

A cozy seating area features a brown leather couch adorned with a floral accent pillow. Two wooden side tables with lamps flank the couch, while a round wooden coffee table with a decorative lace centerpiece occupies the center, set against a rustic wall.

Apartment in Watertown

4.97 out of 5 average rating, 253 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.

Guest favorite

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, 168 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

A cozy cottage exterior is depicted, featuring a wooden deck with a patio table and four chairs, surrounded by lush greenery. Large windows offer views of the outdoor space. The building's log cabin style is complemented by a gravel area and blooming yellow shrubs.

Cabin in Fort Atkinson

4.9 out of 5 average rating, 124 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!

Guest favorite

A spacious living room is presented with a large sectional sofa and a wooden coffee table. Natural light fills the area through multiple windows, while built-in shelves display various decorative items. A flat-screen TV is mounted on the wall above a modern fireplace.

Home in Lake Mills

4.93 out of 5 average rating, 128 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.

Guest favorite

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, 357 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

Two Adirondack chairs are positioned on a grassy area overlooking Lake Koshkongong. The bright blue sky complements the sunlight reflecting off the water, creating a serene waterfront setting.

Home in Edgerton

4.94 out of 5 average rating, 309 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

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, 133 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

The front view of a rustic stone cabin is framed by lush green trees. The structure features a wooden overhang supported by sturdy columns, with large windows allowing natural light to fill the interior. A neatly stacked pile of firewood is visible at the base.

Cabin in Whitewater

4.95 out of 5 average rating, 341 reviews

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.

Top guest favorite

The kitchen features white cabinetry with sleek hardware and a large sink positioned under a window. A tile backsplash adds a modern touch. Ample counter space is available for meal preparation, and kitchen essentials are organized in drawers.

Home in Sun Prairie

4.96 out of 5 average rating, 106 reviews

Nothing Else Like It!

There is absolutely nothing else like it available, and you’ll agree as soon as you step foot inside! This beautifully designed home makes your stay comfortable with it's high end furnishings, bedding, towels, mattresses and dishes. Kick back and relax in this calm, stylish space. Fully fenced backyard great for dogs, entertaining and room for kids to play. Private work space available too! All bedrooms have room darkening shades!