Vacation rentals in Middleton

Cottage Suite + Jacuzzi Tub & 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.

Luxury Lakeside Oasis- 3 Bed / 3 Bath Lake Home

Enjoy time with your loved ones at our luxury lake front oasis. Breathtaking views combined with the ideal Middleton location & extensive updating make our home the perfect vacation destination. Huge windows maximize gorgeous views of 60+ feet of lake frontage. A fully updated kitchen boasts custom everything. Our home features: 3 bedrooms, 3 bathrooms, lofted office, open kitchen with an island & dining table. A short drive (5-7 mi) to UW Campus, Camp Randall, Kohl Center & Wi State Capitol

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

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.

The Wilson L | Quiet Corner Studio with Vanity

Located within The Wilson, this thoughtfully designed second-floor corner studio sits at the back of the building for a quiet, tucked-away feel. Historic charm meets refined comfort, and a dedicated vanity offers a convenient space for getting ready. Guests enjoy access to the shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtfully curated spaces. Second-floor walk-up and paid parking nearby.

The Wilson Unit N | Quiet Renovated Studio

Located within The Wilson, this spacious second-floor studio offers a peaceful stay on the quiet side of the building. Historic charm meets modern comfort with a beautifully renovated kitchen featuring a dishwasher and an updated bathroom. Guests enjoy access to the shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtfully curated spaces. Second-floor walk-up and paid parking nearby.

Peaceful Guest Suite at The Retreat

Looking for a stunning, private retreat in the woods just 10 minutes drive from Epic campus & less than 2 miles from lovely Donald Park? This one-bedroom guest suite over a detached garage is all you need! Airy, modern farmhouse feel with full bath and tiled shower, comfortable queen-sized bed, and tiny kitchenette (mini-fridge, microwave, and hot-plate). Your worries will float away in this ultra-tranquil setting on 10 wooded acres.

The Wright Balance

Find your “Wright Balance” in this cozy lower-level retreat in Middleton Hills, known for its Frank Lloyd Wright–inspired architecture. With a private entrance, two bedrooms, and a full bath, it’s perfect for business, family, or exploring. Just minutes from Madison and UW, yet steps from prairies, wetlands, and trails. Restaurants, a café, and grocery store are all within walking distance—balance convenience with natural beauty.

Private yet close to everything!

Our 900 sqft basement apartment features a master bedroom, connecting kitchenette/sitting room, and bathroom. We are a 20-minute drive to the UW campus, Capitol Square, and Dane County Airport—minutes from Middleton Pheasant Branch Conservancy for hiking and biking. Madison and Middleton consistently win "Best Places to Live" awards for quality of life. As past Superhosts, we are excited to start hosting again after COVID!

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.

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 queen size comfortable 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