Family-friendly holiday rentals in Madison

Gorgeous Eastside Home+Yard+Bikes+5 Star Hosts

This completely renovated, 100-year old home is in the Town of Blooming Grove, an enclave surrounded by Madison's near eastside. It has new heating & air conditioning and is sparkling clean with original hardwood floors, stairs & hardwood trim detail. There are 2 bedrooms (with ample closet & storage space), a living room, dining room, kitchen & bathroom. Please note the staircase is steep and may be difficult for some guests. Please inquire about e-bike availability for use during your stay.

Cottage Suite + Jacuzzi Bathtub & Sauna

This Suite is perfect for 1-5 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond/Bodywash

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.

Lakeview Loft - Downtown Madison

Stay in the heart of Madison, enjoying exclusive access to our 3rd floor suite with lake views. Located on a quiet street along the Lake Loop bike path/Lake Monona, and close to Willy Street (0.3 mi), the Sylvee (1.1 mi), the Capitol (1.7 mi), Monona Terrace (1.6 mi), and Camp Randall (3.3 mi). Self check-in with keypad and ample parking. Wifi is over 500 Mbps download/upload speeds. #ZTRHP1-2022-00022 Note: Loft is accessed by 3 flights of stairs! Space has coffee bar only (no kitchen).

Peaceful, artistic home in the heart of downtown

This inviting, historic home is situated in the most walkable, friendly neighborhood in the city. Just around the corner is a local co-op, loads of quality restaurants, cafes, coffee shops, a park, and easily accessible public transportation. The Capitol and State Street are only about a mile away, making this an ideal location for people in town for business or pleasure. Bright, peaceful, cozy, and outfitted with every convenience in mind, this property will make any guest feel at home.

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.

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!

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, edible cooking supplies are not allowed–we do provide untamperable salt and pepper), 3 bedrooms, 2 full bathrooms, fully stocked laundry room and attached garage!

The Wilson Unit F | Handcrafted Downtown Retreat

Located within The Wilson, this tucked-away third-floor corner studio offers a charming downtown stay. Historic charm meets handcrafted warmth, with woodworking details and cozy design touches. The unit faces the empty lot and may occasionally experience trucks moving gravel. Guests enjoy the shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtful spaces. Third-floor walk-up and paid parking nearby.

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

• 1400 sq. ft. lower level suite • Private backyard with patio • Two TVs • Electric Fireplace • Pool table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • On-site parking in the driveway for one vehicle • Ample street parking • 16-min drive to the UW campus and downtown • 9-min drive to the airport • 6-min drive to shopping and restaurants • Extremely safe neighborhood • License No. LICHMD-2022-00079 • Zone Permit ZTRHP1-2022-00005

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

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.