Holiday rentals in Pittsville

Tiny on the River

According to Forbes, Escape makes "the most beautiful tiny houses in the world". Ours is perched near our home above the Black River. It's a quiet neighborhood just minutes from the interstate, parks, trails, and our vibrant downtown with cafés, shops, and great restaurants. Enjoy privacy and breathtaking views from the enormous windows or the cozy daybed on the porch! Deer, beaver, eagles, and more make frequent cameos as the seasons paint shifting riverscapes and astonishing sunsets. *No Pets

Lake Arrowhead Brown Bear Lodge Sand Valley GOLF

Lake Arrowhead Brown Bear Lodge in Rome WI. 2 HOA golf courses + Sand Valley Golf resort 1.5 miles away. Enjoy all lake Arrowhead offers including Heated private pools (seasonal), 4 private beaches, 2 club houses. Ski Chalet & winter activities. ATV friendly area with miles and miles of trails. This home is also on the Snowmobile trail! Wood burning fire place, lower level wet bar with slate pool table, hardwood floors, new appliances and furnishings. 4 Tvs, wifi and beautiful north woods view!

Stunning Views! - Bunker Hill @HighPointRetreats

Perched in the solitude of nature, our ridge top cabin offers a picturesque view at one of the top elevations in all La Crosse County. Cozy up to your loved ones, relax with friends, or find inspiration in this luxury cabin in the woods. Bunker Hill sleeps four and is non-smoking. Get your front row sunset seats on the private patio and relax by the fire. Immerse yourself in the tranquility and come stay us. *Check out our six other one-of-a-kind retreats listed on Airbnb located in Mindoro, WI

Black sheep cabin with barrel sauna. New build!

Discover peace and style in this brand-new cabin tucked away in the woods—just minutes from the Dells. Modern aesthetic and thoughtful details, this secluded retreat blends natural beauty with upscale comfort. Wake up to birdsong, sip coffee on the private patio, and unwind in a space that feels serene & sophisticated. Whether you're seeking a romantic getaway, a quiet workcation, or a base for Dells adventures, this peaceful woodland hideaway offers the perfect balance of privacy and proximity

Cheerful 2 bedroom cabin with hot tub and pond

This home is just minutes from Lake Arbutus, which has beaches, ATV trails, fishing, boating, swimming, hunting areas and much more. Direct access to ATV/UTV and snowmobile trails! 2 bedrooms with queen size beds; 1 king bed, 1 queen bed and futon in loft. Inflatable kayak and fishing poles for use on the pond or at nearby Lake Arbutus! UTV and Jet Ski rental available on site. We do have a 4 person can-am maverick and 2 Sea Doo jet skis available. Inquire at time of booking for availability.

Driftless Trout Cabin - Hillsboro, Wisconsin

Welcome to our spring-fed cordwood log cabin on 5.66 acres in Wisconsin’s beautiful Driftless region. Enjoy: - World class trout fishing for native brookies or abundant browns - Hiking nearby at the breathtaking Wildcat Mountain State Park or the 8,569 acre Kickapoo Valley Reserve - Canoeing or kayaking the beautiful Kickapoo River - Biking renowned bikes trails through the countryside - Sipping Wonderstate Coffee or Driftless Glen Bourbon on the deck while listening to the babbling spring

River Cottage!

Located in a quiet neighborhood on Lake Petenwell, Wisconsin’s second-largest lake. This cozy well loved 80s-style bi-level home sits on a peaceful canal off the Wisconsin River, offering great fishing just steps from the back door. The upper level features two bedrooms, a full bath, kitchen, living room, and dining area. The lower level includes a family room, additional bed, and hideaway beds on both floors. Ample parking for cars, trailers, and gear makes it perfect for outdoor getaways.

Emerald Little Lodge Overlooking Woodland Pond

Check out Opal Little Lodge also! - - - - - - - - - - - - - - - - - - - - - This cozy modern little lodge designed and built by Wisconsin Tiny Homes, is tucked into the woods 150 ft above a small woodland pond in the valley below. A bird lover's paradise. Comfortably and thoughtfully appointed, it's the perfect getaway to enjoy with a companion or as a solo retreat. Immerse yourself in nature and treat yourself with luxurious accommodations and private hiking trails.

Oasis, NEW Hot Tub, Fire-pit lounge and Coffee Bar

Wild Peak Cottage a newly renovated A-Frame, just a hop, skip, and a jump from Castle Rock Lake, less than 1 mile! Brand NEW hot tub as of 2/18/2026!! Gather around the fire pit, swing on hammocks, roast marshmallows, and create lasting memories. Relax in our large hot tub, under the stars surrounded by pine trees Walking distance (less than 1 mile) to Castle Rock Lake, 25 minutes to Wisconsin Dells, and a short distance to hiking, fishing, wineries, and so much more!

HGTV STYLE Traveling Professionals

Redesigned HGTV style two bedroom home. Home is located just a few blocks off main street, with easy access to our quaint downtown area. Our downtown area has a movie theater, coffee shops, restaurants, bakery, beauty spots, personal health, and shopping. Home is nice and clean. NON SMOKING HOME **** PARKING: per Marshfield Police Department: Nov 1-Apr 30 no overnight street parking. 2:30 am-6:00 am.

Secluded Cabin near the East Fork!

Cozy log cabin on 40 private wooded acres with a south facing wall of windows to enjoy looking at the outdoors. Its off the beaten path, but five miles from the recreational hub of Hatfield, WI and the Black River Forest. We offer a private cabin for up to 4 guests. South Enjoy the outdoors: hiking, canoe/kayaking, ATVing, XC and downhill skiing, hunting, fishing, mountain biking etc.

Grass Creek Getaway: Private, romantic, cozy cabin

Words that past guests have used to describe their stay at Grass Creek Getaway and why I think they chose these words. PRIVATE: located a 1/4 mile off a country road. AMAZING CRAFTSMANSHIP: interior is tediously handcrafted from top to bottom. TRANQUIL: located in wooded area your amongst nature. If you want to get away from the hustle and bustle of everyday life this is the place for you.