Holiday rentals in Village of Cross Plains

Cool, 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.

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

Sugarland Suite

Sugarland Shouse is a unique space in the beautiful driftless area of Southern Wisconsin. It is a one bedroom apartment designed to accommodate up to 5 guests. It has a full kitchen, bathroom with shower, one bedroom with a queen and twin bed. The living area has a pull out queen sized Murphy bed. We are close to the Wisconsin River and only 30 minutes from Madison and 10 minutes from Spring Green home of Frank Lloyd Wright’s Taliesin, American Player’s Theater, and House on the Rock. Edit

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.

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

The Rainbow House *lower-level*

Quiet / peaceful / positive vibes place perfect for a couple but can do one more (twin-size floor mattress / PacknPlay). *NOTE: Must pre-approve pets with initial booking & only booked guests allowed - this is how we feel most safe hosting in our home. No smokers (of any kind) here. Strict quiet hours. My wife Marla and I are so happy to share our sweet sunny lower-level space with you - she built it herself! We live upstairs with our adorable rescue dogs + old aloof cat Tanner.

Historic Luxury Apartment

This luxury 2-bedroom 2nd floor apartment is nestled in a beautifully remodeled historic building originally built in 1860. Combining old-world charm with modern amenities, this apartment offers the perfect blend of comfort and convenience. Located right on the Main Street of Cross Plains, WI, just 25 min away from UW hospital and 35 minutes from downtown Madison. Perfect for families, professionals and anyone looking for a stylish, comfortable stay close to Madison, WI.

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.

Private garden level studio near EPIC

EPIC is a 6 min, traffic free drive. Welcome to our private lower-level flat with a walk-out entrance—ideal for workspace or relaxation. Highlights include: Private bathroom & kitchenette—perfect for light cooking and self-contained convenience. Fully equipped workout gym featuring an Airdyne bike and free weights Two flat screen TV’s for streaming and entertainment. Dedicated office just off the living area—ideal for remote work, study or focused projects.