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

Total vacation rentals
Explore 10 vacation rentals in Middleton

Nightly prices starting at
Middleton vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

Verified guest reviews
Over 530 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Middleton vacation rentals include wi-fi access

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

4.9 Average rating
Middleton stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Middleton
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.
Indoor spacesFamilyAir conditioning

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.
FamilyKitchenWalkability

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!
FamilyKitchenWifi

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.
FamilyIndoor spacesWalkability

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.
Indoor spacesFamilyCondition

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).
Indoor spacesFamilyLayout

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.
FamilyIndoor spacesNearby

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!
FamilyIndoor spacesAmenities

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!
FamilyKitchenTV

Fresh & Bright Apartment Getaway in New Glarus
We would like to welcome you to our bright newly built 2nd floor above garage apartment. Located in a family friendly neighborhood, just a 10 minute walk to downtown where you will find delicious dining, unique shops and historical sites everywhere you turn. Jarod and I with our kids live in the main house. We love giving our guest privacy but may run into you as we are enjoying the weather as often as we can with our kids running around enjoying their childhood.
Indoor spacesFamilyParks

The Dylin Hotel | Studio
● Size: 372 SQFT ● Guests: 2 Guests ● Bed: 1 Queen Bed Experience a thoughtfully designed fully furnished Studio Apartment featuring a fully equipped kitchen, in-unit laundry, Wi-Fi, smart TV and a cozy sleeping area. The Dylin is a modern aparthotel in Madison’s Cap East neighborhood, offering apartment-style comfort with hotel consistency. Perfect for travelers who want more room to relax and live like a local —ideal for short or extended stays.
KitchenIndoor spacesLaundry

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
KitchenFamilyBreakfast
Popular amenities for Middleton family-friendly rentals
Family-friendly home rentals with a hot tub

Sauna | Hot Tub | EV+ | Luxury | Cozy | Private
Indoor spacesKitchenGrill

Relaxing 3 Bedroom Cabin with Hot Tub and Scenery
FamilyIndoor spacesNearby

NEW Hot Tub! Perfect Location, Downtown Baraboo
FamilyIndoor spacesAccess

Big R's Retreat Secluded and located in Nature
KitchenIndoor spacesHospitality

Secluded Patio! Game Room! Fire Pit! Hot Tub!
Indoor spacesKitchenLong stay

Quietwater Cottage-Peaceful, On Water, Sandbars!
FamilyIndoor spacesQuiet

Secluded WI River Getaway w/ Hot Tub near Golfing
KitchenIndoor spacesSkiing

Lake House Summer Getaway
Indoor spacesFamilyParks
Family- and pet-friendly home rentals

YurtSimple
KitchenFamilyBathroom

Nothing Else Like It!
FamilyKitchenPets

2 Bed, 2 Bath Apartment at Cannery Square
KitchenFamilyCheck-in

Historic Randall Schoolhouse
FamilyKitchenDecor

Private DeForest Flat| *Walk to Parks*
Indoor spacesFamilyValue

Prime Time - 3 Bedroom with Fireplace! Sleeps 12
Indoor spacesKitchenWalkability

Cozy Lakefront Cottage With The Best View
FamilyKitchenDecor

Peaceful 2 BR/1 BA w/ patio, fireplace, pool table
Indoor spacesFamilyGrill
Family-friendly home rentals with a pool

Private yet close to everything! NEW
KitchenIndoor spacesHospitality

1BR UpperDells Riverfront: Jacuzzi, Pool & Hot Tub
FamilyIndoor spacesCheck-in

Dells Retreat - Sleeps 8 + Jacuzzi | Waterpark
FamilyIndoor spacesHot tub

Modern Cabin with pool, hot tub and outdoor sauna
KitchenFamilyHospitality

Dells Retreat-A Romantic Haven-Jacuzzi,Pool&HotTub
Indoor spacesKitchenQuiet

Spring Green River Pines
Indoor spacesKitchenHospitality

1BR Professionally Serviced Private Apartment
KitchenIndoor spacesGetting around

HD Jameson House at River’s Edge
KitchenIndoor spacesSleep quality
Destinations to explore
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- Devil's Lake State Park
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- Wisconsin State Capitol
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- Henry Vilas Zoo
- Camp Randall Stadium
- American Players Theatre
- Chazen Museum of Art
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- Madison Childrens Museum
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- Parfrey's Glen State Natural Area
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