Family-friendly holiday rentals in Fitchburg

4.98 out of 5 average rating, 236 reviews

A yurt is depicted, nestled among lush greenery. A wooden deck equipped with two chairs and an umbrella provides seating. The entrance features double doors framed by angled wooden roofing, with a wood-burning stove visible on the side. The surrounding forest offers a sense of seclusion.

Yurt in Cambridge

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

Guest house in Mount Horeb

The exterior of a rustic studio retreat showcases wooden siding illuminated by warm lights at dusk. Large windows offer glimpses of the cozy interior, while kayaks are hung on the side. Surrounding greenery creates a natural ambiance, with a gravel path leading to the entrance.

4.96 out of 5 average rating, 646 reviews

Cool, Roomy, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs, included in your reservation, must be leashed when outside.

4.95 out of 5 average rating, 189 reviews

An A-frame interior showcases a spiral staircase leading to the loft, surrounded by natural wood and brick accents. A large television is mounted above a fireplace, complemented by decorative plants and a wall clock. Colorful patterns can be seen in the ceiling lights.

Home in Arbor Hills

ONE OF A KIND vacation rental with a view

Arbor Hill House - Unique A-frame vacation rental perched atop a hill with great views overlooking the Beltline, UW Arboretum and the city of Madison. Excellent central location with easy access to all of Madison and surrounding areas. I'll be happy to do whatever I can to make your stay a pleasant one. Please keep things clean and be respectful. The home should not be used for parties or events. If you have any questions please feel free to ask. I look forward to sharing my home with you.

4.96 out of 5 average rating, 112 reviews

A cozy living room features a plush orange sofa paired with two gray armchairs. A wooden coffee table is positioned in front, displaying magazines. The room is illuminated by natural light through three windows, and a flat-screen TV is mounted above a decorative fireplace.

Flat in Oregon

Downtown Apt - Steps to Coffee & Sushi!

* Be sure to check out our winter extended stay discounts for 3+ nights! * Welcome to historic downtown Oregon! Step into the past while enjoying modern comfort in this beautiful space, which once housed our 1st library! Just steps away from locally owned coffee and gift shops, a wine reserve, and amazing restaurants! With convenient access to Madison (14 mi), experience the best of both worlds – small-town tranquility and urban excitement. Whether for work or leisure, welcome home!

4.9 out of 5 average rating, 115 reviews

An outdoor dining area is featured on the deck, consisting of a wooden table surrounded by black wicker chairs. A small potted plant adds a natural touch. The scenic view of the river, a bridge, and a private dock can be seen in the background.

Home in Monona

Madison Lakefront Oasis in the Heart of Madison

Enjoy all that Madison has to offer from this beautiful lakefront property. BRING YOUR BOAT, our private dock on Yahara River has 3 slips with access to both Lake Monona & Lake Waubesa. Central location offers multiple restaurants, shops & public boat launch all within walking distance. Breath-taking sunsets over the lake. Quick 5-10 minute commute to downtown Madison, UW-Campus, Hospitals, Alliant Energy & Sylvee, State Street, hundreds of other Madison attractions east or west side!

4.98 out of 5 average rating, 238 reviews

A spacious studio featuring two green upholstered benches arranged on a decorative area rug. Natural light floods the room through skylights, illuminating the cozy sleeping area with a large bed and a dining nook equipped with a small table and chairs.

Guest suite in Middleton

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Guest house in Sun Prairie

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.

4.98 out of 5 average rating, 384 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!

4.91 out of 5 average rating, 131 reviews

This spacious bedroom contains a comfortable bed dressed in white linens, with a decorative throw and pillows. Natural light filters through the window, illuminating a wooden dresser and bedside tables. A textured area rug adds warmth to the room, creating a cozy atmosphere.

Home in Fitchburg

Comfortable Madison Area Retreat In The Trees

Tri-level duplex centrally located in Fitchburg. Nestled in a quiet residential neighborhood backing up to a small patch of woods for privacy. Feel away from it all with the sights and sounds of nature yet close to all the modern conveniences. Enjoy separated living spaces, a fully equipped kitchen (per WI health code, edable cooking supplies, are not allowed–we do provide untamperable salt and pepper), 3 bedrooms, 2 full bathrooms, fully stocked laundry room and attached garage!

4.98 out of 5 average rating, 132 reviews

A scenic view showcases the modern home nestled among vibrant trees on a Christmas tree farm. Rolling hills are seen in the background, adorned with foliage in shades of red, orange, and green. Neatly arranged rows of Christmas trees line the foreground.

Home in Merrimac

Real Christmas Tree Farm! Skiing nearby

Get lost in nature and stay where the magic grows on a real Christmas tree farm! Situated on rolling hills below the Baraboo bluffs, this 125 acre farm and nature preserve has several miles of hike/bike/ski trails, a private lake and two creeks. Modern home in a quiet rural neighborhood. Easy drive on beautiful country roads to the many attractions in the area--less than 10 minutes to Devil's Lake State Park, Lake Wisconsin as well as Devil's Head & Cascade ski areas.

4.98 out of 5 average rating, 142 reviews

A cozy bedroom showcases a spacious bed dressed in a richly patterned coverlet and decorative pillows. A wooden chair is positioned near a bright window, complemented by soft light filtering through sheer curtains. Framed artwork adorns the walls, enhancing the room's welcoming ambiance.

Guest suite in Oregon

Historic Home -Private Apartment

Oregon is a short drive to Madison, Wisconsin’s capital city. Oregon has a budding downtown business district 2 blocks away. Our lower level private apartment is great for couples, friends, families, and business or healthcare travelers. We created the apartment when we built a new addition onto our home in 2014. The apartment has a separate secure private exterior entrance and secure private interior entrance. There is a Ring camera that overlooks the parking area.

4.99 out of 5 average rating, 123 reviews

A bright living space features a gray sofa adorned with a decorative pillow, accompanied by a rounded coffee table. A dining area with colorful chairs and a wooden table is visible in a well-lit room. Natural light filters through the windows, highlighting the modern interior.

Bungalow in Monona

Retro Charm Near DT Madison & Lake Monona

Experience the best of Wisconsin’s Capital City in this newly remodeled 1930's bungalow in one of Madison’s most desirable neighborhoods. Rent a BCycle e-bike and take it for a spin on the famous 13-mile Lake Loop, just steps from our front door. Splash in Lake Monona at nearby Schluter Beach. Treat yourself to an ice cream cone at the retro ice cream parlor. When you're ready to shop or hit the farmer's market, downtown Madison is an easy 15-minute drive.

Superhost

The living room features a large smart TV mounted above a cozy electric fireplace. Two modern sofas and a coffee table are arranged on polished wood floors. A pair of patterned armchairs provides additional seating, complementing the stylish decor.

Townhouse in Fitchburg

4.8 out of 5 average rating, 248 reviews

Clean, quiet & family-friendly Townhouse-14 people

Bright and spacious 3-bedroom, 2-bath duplex perfect for families, groups, or guests with pets. Relax in a large fenced backyard, enjoy the back deck, smart TV, and fully equipped kitchen. Sleeps up to 14 with extra air mattresses and a pack & play. Driveway fits 2 cars, with street parking nearby. Just 10–15 minutes to downtown Madison, Epic, and local attractions. Private, meticulously cleaned, and stocked for a comfortable stay.

Popular amenities for Fitchburg family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Camper van/Motorhome in Hill Point

A spacious camper is positioned on a gravel area, framed by trees. An inviting wooden deck is equipped with seating and large umbrellas, offering shade. A hot tub is located next to the deck, surrounded by landscaping that includes white flowers, creating a serene outdoor environment.

4.94 out of 5 average rating, 151 reviews

Big R’s Retreat 2 Secluded with HOT TUB

4.9 out of 5 average rating, 210 reviews

A hot tub is shown in the foreground, its water illuminated in soft light. Behind, a cottage is visible with large windows revealing a warm, inviting glow. The exterior is adorned with twinkling lights that enhance the cozy atmosphere of the setting.

Home in Poynette

Island View Hideaway-Hot Tub, Near Skiing, Nature!

4.88 out of 5 average rating, 300 reviews

A charming log cabin is nestled among vibrant flowers and greenery. The structure features a large front porch with wooden railings and steps leading to the entrance. Tall trees surround the cabin, offering a natural and serene setting.

Home in Argyle

Relaxing 3 Bedroom Cabin with Hot Tub and Scenery

Cabin in Fontana-on-Geneva Lake

An A-frame structure is nestled among lush green trees, showcasing large glass windows that allow for ample natural light. The contrasting wood siding complements the surrounding foliage, creating a harmonious blend with nature. A raised deck leads to the entrance, enhancing accessibility to the home.

4.93 out of 5 average rating, 172 reviews

Exquisite Modern A-frame all WithInnReach

4.98 out of 5 average rating, 392 reviews

A wooden swing hangs from a tree in a lush green field, gently swaying in the breeze. In the background, the log home is set atop a hill, showcasing its wrap-around deck and panoramic views of the surrounding landscape under a clear blue sky.

Guest house in Stockton

HighviewCountry Escape-log home-family farm w/view

4.96 out of 5 average rating, 180 reviews

The exterior of a green cottage is surrounded by trees, featuring a welcoming front porch with a swing. A small bistro table and two red chairs are visible, complemented by natural landscaping of gravel and stones.

Cottage in Baraboo

Cottage near Devils Lake Baraboo

Superhost

Guest suite in Elkhorn

4.88 out of 5 average rating, 106 reviews

Lake Lovers Hideaway near Lake Geneva

4.99 out of 5 average rating, 205 reviews

The living area features mid-century modern furniture with vibrant green and orange chairs surrounding a coffee table. A gas fireplace is centered under a unique light fixture, and large windows allow views of the surrounding woods. A dining area is visible in the background.

Treehouse in Galena

Octagon treehouse Hottub-pool-fireplace-firepit

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 135 reviews

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

Nothing Else Like It!

4.85 out of 5 average rating, 221 reviews

Home in Bay Creek

House on water! Near UW, Capital & Alliant Center

Place to stay in Brodhead

The exterior of a historic one-room schoolhouse is shown, featuring a red front door and a fenced yard. Surrounding trees provide a natural backdrop, and a shed is visible nearby. Soft sunlight enhances the inviting outdoor space, contributing to a peaceful setting.

4.98 out of 5 average rating, 202 reviews

Historic Randall Schoolhouse

Guest suite in Monona Bay

A bedroom features a spacious bed adorned with a light blue coverlet. Framed artwork decorates the walls, and a bedside lamp provides soft lighting. A small desk and chair are positioned beside the bed, enhancing the room's functionality.

4.98 out of 5 average rating, 638 reviews

DT+Bikes+Pvt Suite+Jacuzzi+Parking+Near Campus

4.86 out of 5 average rating, 116 reviews

The exterior of a modern apartment complex is showcased, featuring a combination of brick and stucco materials. Multiple balconies are visible, with awnings in red and green colors. Surrounding greenery adds to the inviting ambiance of the property.

Flat in Sun Prairie

2 Bedroom - Main Street Sun Prairie WI

4.99 out of 5 average rating, 233 reviews

A cozy seating area features a light gray sofa positioned in front of a mounted TV and an electric fireplace, which emits a calming glow. A decorative plant adds a touch of greenery, while a textured rug and a basket with a towel enhance the inviting ambiance.

Guest suite in Madison

Peaceful 2 BR/1 BA w/ patio, fireplace, pool table

4.9 out of 5 average rating, 156 reviews

A two-story chalet-style building is surrounded by lush greenery. Flower boxes adorn the windows on the upper level, while a sign is visible in the front yard, welcoming guests. The exterior features a combination of dark wood and white siding, set against a clear blue sky.

Flat in New Glarus

Nördlich Chalet - Trail-side, 1 Bdrm in New Glarus

4.86 out of 5 average rating, 153 reviews

A cozy cabin interior features warm wooden paneling and soft lighting. A brick fireplace adds comfort, while a spacious bed is dressed in a patterned quilt. A inviting sofa and round area rugs enhance the welcoming atmosphere of the living space.

Cabin in Brodhead

Cozy Cabin on Decatur Lake

Family-friendly home rentals with a pool

A charming gray house is set against a backdrop of colorful autumn foliage. The front porch features a red door, framed by shrubs and well-maintained landscaping. A clear blue sky provides a bright contrast to the warm tones of the trees.

4.96 out of 5 average rating, 307 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

4.94 out of 5 average rating, 264 reviews

Peaceful, Cozy Home w/ Club Amenities in Galena.

A spacious living area features a navy blue sectional sofa and a modern brown armchair. Large windows provide views of the surrounding greenery. A round, marble coffee table is centered in the room, with a fireplace beneath a mounted television, creating a cozy environment.

4.95 out of 5 average rating, 118 reviews

Cozy Galena Townhome

A round dining table is set outdoors with four yellow plates, each topped with a drink garnished with olives and celery. A bottle of cocktail mix rests beside the glasses, surrounded by textured placemats. Lush greenery provides a natural backdrop.

4.91 out of 5 average rating, 113 reviews

Quiet Yet Close/Steps to Pool/Paths, Pet Free Home

A tranquil vacation home is set in a lush green landscape. The house features a screened-in porch and multiple balconies, surrounded by a wooden fence. Mature trees provide shade, and the inviting lawn enhances the serene outdoor environment.

4.93 out of 5 average rating, 218 reviews

Galena Getaway

An outdoor deck features comfortable seating arrangements, including wicker chairs and a coffee table. Large windows in the background allow natural light to fill the adjacent indoor area while showcasing the surrounding greenery.

4.98 out of 5 average rating, 185 reviews

Covered Hot Tub • 2 Fire Tables • Huge Deck •

Guest suite in Spring Green

A well-maintained home exterior is surrounded by a lush garden, featuring a variety of plants and shrubs. The entrance is framed by a decorative archway, and a large tree provides shade. An inviting walkway leads up to the front door, enhancing the overall charm of the property.

4.91 out of 5 average rating, 172 reviews

Spring Green River Pines