Family-friendly holiday rentals in Middleton

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.

Cottage Suite + Jacuzzi Tub & 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

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.

Private & Clean Apartment Near Downtown & Airport

Private, sunny basement unit with separate entry accessible by keycode. 1 bedroom (queen), full bath, sitting area (2 twins/king bed), desk, WI-FI, TV, mini fridge, microwave, & coffee/tea. On street parking. Kid friendly! Note: We live with kids above the apartment - you will hear us walking around & some water pipes. 2-4 mi from Airport, Capitol, & UW Campus. Walk to brunch, pub, jazz lounge, bubble tea, grocery store, park, & bike path. Licensed by City & State. Paying all taxes & fees.

Private apartment -2 Beds, Kitchen Office, Sunroom

COVID CLEANED Private Garden Apartment. Feel at home in your private lower level living space. Our home is surrounded by beautiful landscaped gardens and patios. We are located near the lake, on the lake bike loop, in the heart of Madison. Relax outside, enjoy dinner on the patio or have a bonfire. Venture out on a bike ride to the farmer's market on the Capital Square, or visit Monona Terrace, State Street, Olbrich Gardens or the Alliant Energy Center; just a short distance away.

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.

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!

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.

Beautiful 3 Bedroom Apartment, Kitchen, Fireplace

Private 3-bedroom lower level 1600sq ft apartment. Follow the path to the back of the main house, here you'll find a beautiful space with large windows and plenty of natural light. Enjoy the warm gas fireplace, large flat screen TV. Make meals in the generous farmhouse kitchen. Sorry no full-size oven. Relax on the paved patio overlooking the wetlands and listen to many birds. Steps away from TPC Wisconsin. Just a 5 min drive to the airport and close to downtown.

Downtown Lake Monona Haven | SUPs, Hot Tub & Sauna

Stay in your private 3BR, 2BA section of our lakefront home. Paddle from the dock, relax in the hot tub or sauna and enjoy mornings on the balcony with coffee. You’re moments from Willy Street restaurants and right on the bike path. Inside, find a full kitchen, comfy living spaces and parking. Spend days on the water or exploring the city and evenings grilling or roasting marshmallows by the fire. Paddleboards included. Pontoon rental available in warmer months.

Private entry flat near Atwood neighborhood

No cleaning fee!! Enjoy your visit to Madison in this sunny one bedroom apartment with private entrance and off street parking. It's great location is within walking distance to the Schenk/Atwood neighborhood, with numerous restaurants, cafes and music venues. Within 2 miles of the state capitol, Monona Terrace, and 3 miles from the airport, Kohl Center and Camp Randall. Perfectly suited for couples, solo adventurers, or business travelers.

Peaceful Guest Suite at The Retreat

Looking for a stunning, private retreat in the woods just 10 minutes drive from Epic campus & less than 2 miles from lovely Donald Park? This one-bedroom guest suite over a detached garage is all you need! Airy, modern farmhouse feel with full bath and tiled shower, comfortable queen-sized bed, and tiny kitchenette (mini-fridge, microwave, and hot-plate). Your worries will float away in this ultra-tranquil setting on 10 wooded acres.