Holiday rentals in Cross Plains

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.

Dells Domes - Riverview Escape - Glamping Dome 4

Staying in a dome amidst nature is a unique experience. The circular structure offers an amazing view of the surroundings, with peaceful sounds of rustling leaves, chirping birds, and a flowing river below. The cozy dome has a queen size bed, night stands, a seating area, mini fridge, and a k-cup coffee maker & heater/ac. At night, the starry sky and nature's sounds lull you to sleep. Waking up, you feel refreshed, and the peaceful surroundings and breathtaking views leave a lasting impression.

Cottage Suite + Jacuzzi Bathtub & 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

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Bo and Aero's Retreat

Bo and Aero's retreat is named after the two friendly(and quiet) Labradors that live upstairs. Located in a quiet neighborhood within walking distance to a historic downtown. If biking, hiking, running, walking, snowshoeing or cross country skiing are part of your routine we are located just off Military Ridge trail,near Blue Mounds and Governor Dodge State Parks. We are 30 min from downtown Madison.This is a home away from home. Perfect for long term rental and traveling medical staff.

Haney's Tavern

Haney's Tavern (an INN) built from native stone, erected for Berry Haney in 1840, was a well-known Stagecoach Stop (on Stagecoach Road today) for weary travelers off the Military Trail. This unique historic property is beautifully situated at the Gateway to the Driftless Region and along the Cross Plains Segment of the Ice Age National Scenic Trail. The serene Black Earth Creek, a Class 1 Trout Stream meanders through the acreage. Make memories at this unique and family-friendly place.

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

Nestled in the country, this luxurious home offers a serene escape from the hustle of city life. Enjoy two spacious bedrooms and two meticulously designed bathrooms featuring indulgent amenities, such as a deep soaking tub. A cozy living area with a stone fireplace invites relaxation, while a gourmet kitchen beckons culinary adventures. Outside, soak in the hot tub, grill up some dinner, share stories around the fire, or watch the sunset from the sauna, all amidst nature's embrace.

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.

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!

Cozy Cabin in The Driftless

This cozy cabin in the woods is located atop the beautiful rolling hills of the Driftless area, just outside of Cross Plains, WI. Nestled on 10 acres of forest, this warm rental is the perfect getaway for a private winter weekend away, a nature/yoga/artist retreat, or a road biking vacation. Located just 30 minutes from downtown Madison, Wisconsin's capital city. Base rate for up to 4 guests, additional guest fee applies for each guest over 4. Minimum stay of 3 nights.

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.

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!