
House holiday rentals in Middleton
Find and book unique houses on Airbnb
Top-rated house rentals in Middleton
Guests agree: these houses are highly rated for location, cleanliness and more.

House on water! Near UW, Capital & Alliant Center
Enjoy a drink while sitting in the living room, looking out over Monona Bay & the Capital. What is better?--the view, or your proximity to downtown, UW campus, & the Alliant Center? Most mention the view. (Read some reviews!) Grill out and light the fire pit on the front lawn. Cross the street, and you're at the edge of Monona Bay. Parking is easy. Click “Show more” for things you might NOT like about the house: I'll be in the basement, pricing nuances, etc. Business travelers?--read on!

Cottage Near Devil's Lake
Perfect Location! Under ten minutes to almost everything. Our cozy and romantic getaway is nestled in the scenic Baraboo Bluffs, just minutes to Devil's Lake, Devil's Head Resort, Historic Downtown Baraboo, wineries, distilleries & more. Take the picnic set to Devil's Lake or Parfrey's Glen, then relax on the patio for smores and yard games around the fire pit. Finish the evening snuggled up with wine & vinyl on the player. We have ample parking so bring the boat, we'd love to help you getaway.

4-Bedroom Lathrop Home by UW/Camp Randall -Madison
Home steps to Camp Randall & a short walk to UW Madison! $375 / night (up to 5 guests); Extra guests $75 / night after the 5th guest ($1045 Nightly Rate up to 10 people max) $495 / night during Badger game days (up to 5 guests; $65 / night / guest after the 5th guest) Our back patio is also available to guests; however, please know that we use the garage & part of the driveway for tailgating with friends & family during Badgers football games. Cleaning Fee $150. No Pets or Smoking allowed.

Grooviest | Quiet | Close | Upscale MCM | Records!
• NEWLY RENOVATED SPACE. • Two floor upper unit in a private home • Private backyard with patio & fire pit • Flatscreen TV in living room with Chromcast and Antenna. • Luxury Mid Century Modern Stereo Console bluetooth • 12+ classic albums to listen to (jazz, rock, classical) More Avail Locally! • Access to thousands of albums at several nearby vintage vinyl stores • Electric fireplace w/ multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked, Keurig • Vintage Bar Cart

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.

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).

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.

Richard's House
Permit Number ZTRHP1-2020-00480 Sunny five-six bedroom house plus sleeping porch, large living, dining, family rooms, and dinette. Large deck, patio, and outdoor sitting area. Conveniently located on Madison's west side(just off University Ave.) on very large wooded lot. The house is 10.9 miles from EPIC, a straight shot to DOWNTOWN Madison via University Avenue and an easy drive from the AIRPORT going around the north side of Lake Mendota. Parties and events are not allowed.

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!

Cozy, Sunny Artist's House (UW/Near West)
Our historic, art-filled home is close to the UW hospital and campus, but is located in a quiet and pretty neighborhood. Madison is known for its open-mindedness, amazing farm-to-table restaurant scene, walk- and bike-ability, and lots of performing arts for the small size of the city. We're Superhosts in our tenth year and we'd love to comfortably accommodate you. Please take the time to read our entire listing if you'll be staying with us to learn details about the house.

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!
Popular amenities for house rentals in Middleton
House rentals with a pool

Comfortable 4 Bed 4 Bath in the Galena Territory!

Peaceful, Cozy Home w/ Club Amenities in Galena.

Cozy Galena Townhome

Dells Retreat | Family Friendly Sleeps 8 + Jacuzzi

Fox Wood Retreat | Hot Tub + 12PM Check-In

Covered Hot Tub • 2 Fire Tables • Huge Deck •

Lake Views | Hot Tub | Nature Retreat | Movie Room

HD Jameson House at River’s Edge
Weekly house rentals

Lake + HotTub + PrivateDock + SmartTV + GameRoom + EVCharger

Cottage gem: Spotless, secluded & bring the dog!

Haney's Tavern

Lake Landing

Downtown Verona: Cozy Hideaway

Bohn Road Farmhouse

Stone Farmhouse Stay

Historic guesthouse near UW
Private house rentals

Madison's First EcoLodge

The Orchard House

Shorewood Hills Modern Home

NEW Build! 2BR Cozy Cove | Minutes to Madison

Two Private Floors in Secluded Home

Hollandale Haven

The Kosh: lake life & relaxation!

Historic Downtown House Overlooking Park and Lake
Quick stats about house rentals in Middleton

Total holiday rentals
Explore 10 holiday rentals in Middleton

Nightly prices starting at
Middleton holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 510 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Middleton holiday rentals include wifi 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!
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
- Ann Arbor Holiday rentals
- Traverse City 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
- Cascade Mountain
- House on the Rock
- Henry Vilas Zoo
- Wollersheim Winery & Distillery
- Kohl Center
- Chazen Museum of Art
- Madison Childrens Museum
- Overture Center For The Arts
- Governor Dodge State Park
- Dane County Farmers' Market
- Camp Randall Stadium
- Monona Terrace Community And Convention Center
- American Players Theatre




