Family-friendly vacation rentals in Middleton

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

Stay With Horses Equestrian 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

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! Good dogs in your reservation must be leashed outside, kenneled when you’re away.

Private guest suite on beautiful Lake Mendota

Cozy guest suite/basement apartment with separate entrance for nature lovers. Lake and capitol views from breakfast nook with microwave and mini fridge and coffeemaker. Full kitchen coming fall 2025. Quiet, woodsy, neighborhood adjacent to Governor Nelson State Park. Completely painted and updated 7/25/24. Tiki level, pier, and kayaks for guest use. People love the views, the hot tub and woods. It is a 1929 cabin so many stairs, some indoor insects and limited space. Well behaved pets welcome!

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

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!

Campo di Bella Winery & Family Farm LLC

Welcome to Campo di Bella Farmstay. We have created a private retreat above our winehouse on our farm. You will enjoy the sights and sounds of country living. Weekend Farm to Table dinners available on-site and we typically reserve seating for our farmstay guests. From December to end of March, we are only offering dinners on Friday nights. Max room rate $175.00. Please note that during winter months, we are on a private road and snowplowing may be completed by early afternoon.

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!

Luxurious & Spacious 4 BR Home w/o Cleaning Fees

Escape to our stunning Madison home! Luxuriate in the sleek contemporary design, spacious living areas with high-end finishes and tasteful furnishings. Unwind in the comfortable bedrooms with ample storage. Step outside to our backyard oasis for al fresco dining and relaxation. Our exceptional customer service and thoughtful touches guarantee an unforgettable stay. Close to Madison's best shopping, dining, and entertainment. Book now for an experience you won't forget!

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.

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!