
Family-friendly holiday rentals in Middleton
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Middleton

Total holiday rentals
Explore 20 holiday rentals in Middleton

Nightly prices starting at
Middleton holiday rentals start at $76 SGD per night before taxes and fees

Verified guest reviews
Over 560 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Middleton holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Middleton rentals

4.8 Average rating
Middleton stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated family-friendly rentals in Middleton
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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

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

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 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!

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!

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!

Downtown Verona Hideaway
Your own beautiful 2 bedroom 1 bath (850 sqft) on quiet street in bustling downtown Verona. Washer/dryer in unit with off street parking spot and lots of street parking. Freshly painted with new flooring throughout. Walking distance to restaurants, bars, shopping, library, Farmer Market etc. There are 2 queen beds, one in each bdrm. The couch also pulls out and up to make a bed. Just a few miles away from Epic.
Popular amenities for Middleton family-friendly rentals
Family-friendly home rentals with a hot tub

Island View Hideaway-Peaceful, On Water, Sandbars!

Family Fun! Hot Tub•Fire Pit•Game Room•3 Kings!

Hot tub,Fireplace,Pool/Marina Access,Games, Space!

Relaxing 3 Bedroom Cabin with Hot Tub and Scenery

Hot Tub | Fireplace | Screened Porch | Pool Access

Exquisite Modern A-frame all WithInnReach

NEW Hot Tub! Perfect Location, Downtown Baraboo

Lake Lovers Hideaway near Lake Geneva
Family- and pet-friendly home rentals

Wild Rose Ranch Guest house

Peaceful Guest Suite at The Retreat

Country cabin, birders paradise.

Vast Lake Koshkonong Views from Pier, Deck, & Home

Historic Randall Schoolhouse

Prime Time - 3 Bedroom with Fireplace! Sleeps 12

Quiet Waterfront 2BR w/Dock & Huge Patio

Cozy Cabin on Decatur Lake
Family-friendly home rentals with a pool

Hot tub/Game Room/Fire Pit/Across street from Pool

Galena Getaway

Dells Retreat | Family Friendly Sleeps 8 + Jacuzzi

Spacious Pine Cabin on Lake Delton

Awesome Lodge in Galena Territory

Aspen House - A Secluded Getaway In Nature

HD Jameson House at River’s Edge

Wildlife Surrounds this Stunning Log Home!
Destinations to explore
- Chicago Holiday rentals
- Upper Peninsula Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Minneapolis Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Minnesota River Holiday rentals
- Traverse City Holiday rentals
- Ann Arbor Holiday rentals
- Twin Cities Holiday rentals
- Devil's Lake State Park
- Glacier Canyon Lodge
- Noah's Ark Waterpark
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Mirror Lake State Park
- House on the Rock
- Cascade Mountain
- Wollersheim Winery & Distillery
- Henry Vilas Zoo
- Kohl Center
- Governor Dodge State Park
- Overture Center For The Arts
- Chazen Museum of Art
- Camp Randall Stadium
- Dane County Farmers' Market
- Monona Terrace Community And Convention Center
- American Players Theatre
- Madison Childrens Museum
- Alliant Energy Center





