Holiday houses in Cross Plains

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Top-rated holiday rentals in Cross Plains

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Top Guest favourite
The dome structure glimmers in the moonlight, surrounded by tall trees that create a serene ambiance. A warm glow from a nearby fire pit reflects off the dome's surface, enhancing its unique design. The wooden platform adds a cozy touch to the natural setting.
Dome in Wisconsin Dells
4.97 out of 5 average rating, 182 reviews

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.

Superhost
A view from the breakfast nook captures a sunset over Lake Mendota. The serene water reflects hues of orange and gold, while a grassy area and few remnants of snow are visible. A coffee maker and glass kettle rest on the windowsill, enhancing the cozy setting.
Guest suite in Waunakee
4.81 out of 5 average rating, 329 reviews

Private guest suite on beautiful Lake Mendota

Cozy guest suite/basement apartment with separate entrance for nature lovers. Lake and capitol views from breakfast nook with microwave and mini fridge and coffeemaker. Full kitchen coming fall 2025. Quiet, woodsy, neighborhood adjacent to Governor Nelson State Park. Completely painted and updated 7/25/24. Tiki level, pier, and kayaks for guest use. People love the views, the hot tub and woods. It is a 1929 cabin so many stairs, some indoor insects and limited space. Well behaved pets welcome!

Top Guest favourite
Home in Madison
4.97 out of 5 average rating, 268 reviews

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).

Top Guest favourite
An open-concept living space is captured, featuring a modern kitchen, a dining table, and a stone fireplace. The cozy seating area invites togetherness. An inviting hot tub sits on a covered deck, surrounded by trees. A sauna made of warm wood offers an additional relaxation option.
Cabin in Baraboo
4.98 out of 5 average rating, 112 reviews

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.

Top Guest favourite
A spacious studio featuring two green upholstered benches arranged on a decorative area rug. Natural light floods the room through skylights, illuminating the cozy sleeping area with a large bed and a dining nook equipped with a small table and chairs.
Guest suite in Middleton
4.98 out of 5 average rating, 267 reviews

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.

Superhost
A charming cabin is nestled among lush greenery, showcasing a stone and wood exterior. Large windows allow natural light to flood the interior, while a wooden deck is visible, surrounded by nature. The inviting entrance features a staircase leading to the upper level.
Cabin in Cross Plains
4.74 out of 5 average rating, 112 reviews

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.

Top Guest favourite
The open living area features a light-colored sectional sofa and a coffee table at its center. A dining table with wooden chairs is visible on one side, while a kitchen with modern appliances and green accents can be seen in the background. Natural light illuminates the space through large windows.
Apartment in Cross Plains
4.99 out of 5 average rating, 67 reviews

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.

Guest favourite
Cabin in Merrimac
4.92 out of 5 average rating, 273 reviews

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!

Top Guest favourite
An outdoor deck features a cedar hot tub and seating area, surrounded by natural landscapes. In the background, a fire pit is set up with chairs, while a picturesque sunset casts a warm glow over the serene surroundings.
Cabin in Viola
4.99 out of 5 average rating, 174 reviews

Secluded cabin,cedar sauna & hot tub,outdoorshower

360 views in the middle of 75 organic acres, no neighbors in site. Outdoor Cedar hot tub & infrared sauna, heated outdoor shower, two king loft bedrooms, full kitchen, back deck with custom hibachi grill to watch sunrise and front covered deck to watch sunset. Indoor/ outdoor fire places. Wildflower fields.We try to give our couples priority booking when they rent our wedding venue 2 miles down the hill (Chapters on the Horizon) that is why we do not instant book.

Top Guest favourite
An open living area features a comfortable gray sectional sofa and a coffee table. A dining table for four is visible, accompanied by white chairs. Natural light fills the space through a window, while green plants and modern decor add a touch of freshness.
Guesthouse in New Glarus
4.98 out of 5 average rating, 306 reviews

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.

Top Guest favourite
The kitchen features white cabinetry with sleek hardware and a large sink positioned under a window. A tile backsplash adds a modern touch. Ample counter space is available for meal preparation, and kitchen essentials are organized in drawers.
Home in Sun Prairie
4.97 out of 5 average rating, 157 reviews

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!

Top Guest favourite
A spacious dining area features a rectangular table set with a checkered tablecloth and surrounded by blue chairs. A decorative arrangement of flowers sits at the center of the table, and a patterned rug adds warmth to the space. Shelving with books is visible in the background.
Guest suite in Madison
4.94 out of 5 average rating, 421 reviews

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 comfortable queen size 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

Popular amenities for Cross Plains holiday rentals