Holiday rentals with breakfast in Madison

Red Lodge-Lake Nearby w/Game Room, Hot Tub!

Conveniently located amidst Southeast Wisconsin's best attractions, The Red Lodge is a contemporary-styled retreat that offers the space and family-friendly amenities to keep everyone entertained for hours. Enjoy an arcade game room, a secondary game area, hot tub, fire pit, BBQ area, and more! Rent a boat right in the neighborhood at Lauderdale Lakes. Bike and hike Kettle Moraine State Forest. Visit Lake Geneva for golfing and shopping-a quick 20-25 min drive. Alpine Valley is minutes away!

Two Private Floors in Secluded Home

Exclusive use of top 2 floors of home in a scenic location. Host will reside solely in basement apartment during your stay. Location is perfect as a base for exploration. 5 minutes from Governor Dodge State Park. 8 minutes to The House On The Rock. Also close to Taliesin, American Players Theater, Spring Green and Mineral Point. Or, you can just get away from it all by enjoying this scenic location at the end of a long private driveway. If you enjoy solitude, this is the place for you!

Peaceful, artistic home in the heart of downtown

This inviting, historic home is situated in the most walkable, friendly neighborhood in the city. Just around the corner is a local co-op, loads of quality restaurants, cafes, coffee shops, a park, and easily accessible public transportation. The Capitol and State Street are only about a mile away, making this an ideal location for people in town for business or pleasure. Bright, peaceful, cozy, and outfitted with every convenience in mind, this property will make any guest feel at home.

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.

Rural Driftless Region Stay with Pastoral View

Comfortable country decor highlights a 2nd floor view of the secluded farmstead including summer vegetable gardens, outdoor cats, and an Aronia berry orchard. A mile's worth of hiking or silent winter sports trails meander throughout the property; perfect for discovering songbirds, wildlife; unwinding & connecting with nature. Nearby tiny rural towns host seasonal events; enhancing the pastoral & bucolic atmosphere. The rolling hills offer rewarding biking experiences.

Fun Family Summer!<-Hot tub-Firepit-Game room->

Enjoy the ultimate summer retreat at our stylish 4-bedroom cabin in Galena Territory! Sip your morning coffee on the deck, then explore nearby trails or relax in the hot tub. Challenge family and friends to arcade games, air hockey, darts, and board games. With 10 amenity cards, access the Owner’s Club for swimming, fitness, and indoor pickleball—rackets and balls provided! Whether you seek adventure or relaxation, this cabin is your perfect summer getaway!

NEW! Boutique Inspired 2BR Loft, Lake Geneva

Rest. Play. Recharge. Whatever your soul needs. Dance to your favorite record, sip homemade lattes, share personal stories, host intimate dinner parties. TheUpperHalfLoft, a boutique-inspired space, situated above a locally owned cheese-tasting bar (wine pairings encouraged) and just a short stroll from the heart of Downtown Lake Geneva. Truly the best of both worlds — the energy of a get-a-way town and the restfulness of a quiet place to land.

Modern large home tucked away. 5 bedrooms, 6 beds.

Enjoy your stay which is 5 minutes from the east side of Madison, 2 minutes from Cottage Grove, 5 minutes from Sun Prairie. 2-minute drive to the Oaks Golf Course (4.5-star golf course.) Right off Hwy 94 and Hwy N. There is a small creek that goes through the backyard and the homes are far apart. Sleeps 8 people. 1 King Bed, 2 Queen beds, 1 double bed, 1 twin bed. There are smart tvs in 4 of the rooms. Free wifi with tesla charger.

Dell Prairie A-Frame Chalet

Visit the Wisconsin Dells area and relax in a nature inspired, chalet-in-the-front and a-frame-in-the-back. Located 10 minutes from downtown Wisconsin Dells near Fawn Lake. This unique home is truly a work of art, designed and decorated intentionally for guests to enjoy and be inspired by. Enjoy your morning coffee on the large deck or sit around the campfire while watching the wildlife and planning your Dells adventures.