Holiday rentals in Waterloo

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Top-rated holiday rentals in Waterloo

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Yurt in Cambridge

4.98 out of 5 average rating, 265 reviews

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

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Guest favourite

A neatly arranged bedroom features a spacious bed with soft linens and accent pillows. Natural light fills the room through two large windows. A small bedside table with a lamp stands next to the bed, and a vintage-style ladder is positioned at the foot of the bed.

Home in Marshall

4.93 out of 5 average rating, 107 reviews

1898 Farmhouse on 75 acres - MJ's Farm

Nestled down a winding country road, relax and unwind on a traditional Wisconsin farm surrounded by a 2,296 acre Wildlife Area. Our farmhouse is licensed by Dane County & a short 20 minute drive to Madison! You will want a car so you can explore, the UW Campus, Allient Energy Center, WI State Capitol, Madison Farmers Market and much more. Relax, unwind, grill, play horse shoes or sit by the fire pit. Enjoy your privacy but know there is a farm manager close by and I am happy to help

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Top guest favourite

Farm stay in Cambridge

4.99 out of 5 average rating, 113 reviews

Stay With Horses Escape Near Madison

Get ready for a quiet and peaceful stay. Take your pick: - 1King+1Queen Bed & 1 bath for 4 people - 1King+2Queen Beds & 2 baths for 6. (+$125 per night, contact host for payment) This home is attached to a barn with 6 Icelandic horses! Wake up to Icelandic horses just outside your window. A scenic escape with quiet mornings, fuzzy horses, and a one-of-a-kind IamGlytja experience - only 25 minutes from Madison - No horse riding allowed, owners to supervise all horse visits - No smoking / parties

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Top 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, 202 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.

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Top guest favourite

The two-story house features a grey exterior with a gabled roof and decorative shingles. A welcoming front porch is adorned with seasonal decorations, including small pumpkins. A well-maintained lawn and a stone pathway lead to the entrance, surrounded by lush greenery and trees.

Home in Lake Mills

5 out of 5 average rating, 37 reviews

The Yellow Door Guest House-Lower

Welcome to this turn of the century 2 story home where West Coast cool meets Midwest mod and is the hippest place in town. Two separate apartments available. Located in a convenient, friendly, residential neighborhood, curated with midcentury decor and curiosities, spacious rooms, and an old world charm with a big backyard and firepit. Your favorite space will undoubtedly be “the cabin” as you sip your coffee and tea, and plan your day. You just might want to live here! Adults only!

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Guest favourite

Cabin in Fort Atkinson

4.92 out of 5 average rating, 180 reviews

Cozy Lakefront Cottage With The Best View

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!

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Top guest favourite

Place to stay in Waterloo

5 out of 5 average rating, 12 reviews

The Loft at River's Edge

Stay in our beautifully renovated loft above The Venue at River’s Edge in downtown Waterloo. This private upstairs apartment blends historic charm with modern comfort—perfect for couples, wedding guests, or weekend travelers. Just steps from the scenic Menausha River, shops, and dining. Relax upstairs after events, and experience a unique stay with character, convenience, and style. Ideal for those seeking comfort and easy access to local attractions. Just 25 minutes from Madison!

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Top guest favourite

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.

Guest house in Sun Prairie

4.98 out of 5 average rating, 406 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!

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Top guest favourite

A bright dining area is highlighted by a wooden table surrounded by chairs. A chandelier hangs above the table, while natural light enters through sliding glass doors leading to an outdoor space. A nearby console table displays decorative items, enhancing the open atmosphere.

Home in Cambridge

4.94 out of 5 average rating, 105 reviews

Quiet country retreat

Peaceful solitude or exciting sightseeing? You’ll have the best of both worlds at this quiet country home located just outside Madison on 10 magnificent acres. After, enjoying your morning coffee, take a stroll on the grounds and enjoy the sweeping views of the pastoral landscape. Then head into Wisconsin’s state capital (23 minutes by car) for an exciting day of sightseeing. Or visit the quaint town of Cambridge (8 minutes by car) to explore its unique pottery and antique shops.

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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

4.96 out of 5 average rating, 177 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.

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Top guest favourite

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

4.97 out of 5 average rating, 159 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!

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Guest favourite

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

4.94 out of 5 average rating, 145 reviews

Rock Lake Retreat - Lake Mills Wisconsin

Welcome to Rock Lake Guest House, a serene lakeside retreat on the shores of Rock Lake, just minutes from charming, legendary Lake Mills. This light-filled, updated home offers a private wooded escape with treetop and lake views from every room. The cozy living room features built-ins and opens to a wraparound deck overlooking the water—perfect for relaxing in this peaceful, all-season getaway.

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