Family-friendly holiday 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

Family · Kitchen · View

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.

Family · Indoor spaces · Outdoor spaces

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!

Family · Indoor spaces · Nearby

Cottage gem: Spotless, secluded & bring the dog!

Bring the whole family - furry friends, too! - to relax beneath towering trees in our quiet cottage on Madison's west side. Cooks love the refreshed kitchen with all the tools! Enjoy a remodeled bathroom, Mid Mod furnishings & comfy beds. Grill & dine on a spacious deck and enjoy the wooded (unfenced) yard. Dog owners: Up to 2 well-behaved pooches are welcome with $125 pet fee at booking; please observe rules so we can keep hosting 4-legged friends and maintain a pristine home for all guests.

Kitchen · Indoor spaces · Decor

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.

Kitchen · Family · Condition

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).

Family · Indoor spaces · TV

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.

Family · Indoor spaces · Breakfast

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!

Family · Kitchen · Heating

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. Two parking spots included. 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.

Indoor spaces · Kitchen · Nearby

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.

Indoor spaces · Family · Condition

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!

Family · Indoor spaces · Checkout

Far Westside Home Away From Home

Your own 820 square foot space with full bathroom. Located 6.2 miles from the UW Madison. Inside, you will find a bedroom with a queen bed, living room w/a comfortable queen size sofa bed, a 54”HDTV, a kitchenette (not a full kitchen) w/a dining room table, a mini-fridge, and a library. To see a video of the space go to YouTube and search on “v=hDgEasBTxoA” (cut and paste recommended). ZTRHP1-2020-00044

Family · Kitchen · Hot tub