Vacation rentals in Cross Plains

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Top-rated vacation rentals in Cross Plains

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite

A comfortable living area features a black leather sofa adorned with red and yellow pillows. A wooden coffee table sits in front, and a colorful area rug adds warmth to the space. The background reveals a well-lit kitchen with modern fixtures.

Home in Madison

Charming Campus Area Home • Entire Home Near UW

Steps to Camp Randall & an easy walk to UW–Madison! Spacious home for up to 10 guests with a comfortable layout, multiple bedrooms, full kitchen, and inviting gathering spaces. Enjoy the back patio—perfect for unwinding after a day on campus or exploring the city. Ideal for Badgers game weekends, family visits, and group stays. Please note: during football weekends, the host may use the garage and part of the driveway for tailgating; parking may be shared. Cleaning fee $150. No pets or smoking.

ValueFamilyBackyard

4.98 out of 5 average rating, 285 reviews

Guest favourite

A serene outdoor seating area is highlighted by four wicker chairs arranged around a round table. Lush greenery surrounds the space, and views of the tranquil lake create a peaceful atmosphere. A subtle path leads toward the water's edge, with distant docks visible.

Home in Middleton

Luxury Lakeside Oasis- 4 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: 4 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

FamilyLocationAccess

5.0 out of 5 average rating, 20 reviews

Guest favourite

A two-story farmhouse is framed by two large trees and surrounded by lush greenery. The entrance features a blue door with a decorative wreath, leading to a welcoming facade. Soft sunlight illuminates the front yard, highlighting the manicured lawn.

Home in Mount Horeb

Bohn Road Farmhouse

Located in the valley of the Town of Vermont and just a short drive from downtown Mt. Horeb, our charming and cozy farmhouse offers the perfect retreat for family and friends. Situated on numerous bike baths and a walk across the street to Tyrol Basin, you will be just minutes away from top outdoor destinations like Blue Mounds State Park and Cave of the Mounds. Epic Campus, Downtown Madison, American Players Theatre, New Glarus Brewing, and House on the Rock are all under a 30 minute drive.

LocationValueCondition

4.93 out of 5 average rating, 30 reviews

Top guest favourite

A two-story brick house is situated on a lush green lawn, surrounded by tall trees and shrubs. The exterior features a sloped roof and multiple windows catching natural light. Steps lead to a welcoming front entrance, complemented by a clear blue sky dotted with clouds.

Home in Mount Horeb

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.

LocationValueCondition

4.86 out of 5 average rating, 129 reviews

Top guest favourite

The historic inn features a blue exterior with a spacious front porch adorned with white railings, highlighted by decorative red, white, and blue accents. Lush green grass surrounds the property, with several flowering plants positioned near the foundation, under a clear blue sky.

Home in Cross Plains

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.

ValueLocationCleanliness

5.0 out of 5 average rating, 26 reviews

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

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.

FamilyLocationWalkability

4.98 out of 5 average rating, 278 reviews

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

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.

FamilyValueComfort

4.99 out of 5 average rating, 74 reviews

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

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.

LocationValueNearby

4.73 out of 5 average rating, 113 reviews

Guest favourite

Cabin in Merrimac

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!

LocationFamilyOutdoor spaces

4.92 out of 5 average rating, 284 reviews

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

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!

LocationValueBathroom

4.97 out of 5 average rating, 170 reviews

Top guest favourite

Home in Middleton

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.

FamilyLocationQuiet

4.97 out of 5 average rating, 37 reviews

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

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

LocationFamilyCheck-in

4.94 out of 5 average rating, 429 reviews