Holiday rentals in Pittsville

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Top-rated holiday rentals in Pittsville

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Top guest favourite
A modern tiny house is set within a lush green yard, featuring wooden siding and a metal roof. Large windows provide views of surrounding trees and landscaping. Decorative stones and plants enhance the outdoor space, while a wooden deck offers an entryway to the home.
Tiny home in Black River Falls
4.97 out of 5 average rating, 443 reviews

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

Top guest favourite
A log cabin-style home features a wide front deck with sturdy railings, complemented by large windows that allow natural light to flood the interior. A stone chimney and well-maintained landscaping add to the inviting exterior.
Cabin in Nekoosa
4.9 out of 5 average rating, 118 reviews

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!

Guest favourite
An inviting log home is set amidst a natural landscape, surrounded by trees showcasing autumn colors. A fire pit with stone edging is complemented by several red Adirondack chairs arranged around it. The spacious yard offers ample outdoor space for relaxation and gatherings.
Home in Arkdale
4.94 out of 5 average rating, 100 reviews

Cozy Hideaway

Kick back, Unplug. Connect with nature and enjoy this calm, cozy and relaxing place. Over 1,000 sqf of log home on 8 acres of pure nature, Bring your boat or watercraft to use on many nearby lakes or enjoy a day at the beach (10 min away), many state parks in the area. Fish, hike, bike, swim. The outdoor recreational opportunities are endless. Bring your snowmobile or ATV. Property will satisfy anything from a romantic getaway, family get together, or simply taking a few days off to recharge. --

Top guest favourite
Cabin in Adams
4.94 out of 5 average rating, 457 reviews

Cozy Log Cabin in the Woods

Adams County TRH License #7333 Welcome to the Lucky Dog Cabin! Nestled in the trees, our charming log cabin is located 25 minutes North of the Wisconsin Dells and less than 10 minutes from Castle Rock Lake, Wisconsin River, and Quincy Bluff State Park. Come relax, unplug, and get away from it all. Enjoy the fresh air, starry nights, and peaceful nature sounds. Our 9 acre property offers a beautiful trail that leads to gorgeous sunset views, through the forest. A true nature-lover's paradise!

Guest favourite
A serene winter scene is presented, showcasing a snow-covered landscape with a view of the Wisconsin River at sunset. Trees frame the image, and a deck is visible in the foreground, offering a peaceful space to enjoy the natural beauty and vibrant colors of the sky.
Home in Nekoosa
4.97 out of 5 average rating, 182 reviews

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.

Top guest favourite
A spacious studio apartment is highlighted by a large, unique chandelier above the bed. Natural light floods the area through multiple windows, illuminating the polished wooden floors and cozy seating arrangement. The open layout includes a kitchenette visible in the background, enhancing the inviting atmosphere.
Loft in Amherst
4.96 out of 5 average rating, 172 reviews

Tiny Town Bakery Flatlet

Ever wanted to see what goes on in a commercial bakery? Imagine waking to the aroma of baking bread and cinnamon rolls? Get a bird's eye view into the kitchen of the Village Hive Bakery Kitchen while staying in the newly renovated "flatlet". Salvaged & repurposed building supplies used to create a unique studio apartment above the bakery retail. Guests can enjoy the retail farmhouse table and comfortable seating space by the Main Street picture window. Cooking/baking classes available.

Top guest favourite
A spacious living area features a black leather couch, a round wooden coffee table, and a colorful area rug on hardwood floors. A flat-screen TV is mounted above a brick fireplace, with large windows framed by green curtains allowing natural light to fill the room.
Home in Marshfield
4.95 out of 5 average rating, 213 reviews

Modern space with historic charm

Make this cozy historic, 2100 square ft home your respite while in Marshfield. Whether in town for business or pleasure, you will be a mile or less from shopping areas, downtown and the medical complex. In a safe and quiet neighborhood, across from Columbia Park, you are sure to start your day off right with a cup of hot coffee/tea. Prepare meals in the large kitchen and eat at the dining room table to share the day's events. Then get tucked into soft cotton sheets to drift off to sleep.

Top guest favourite
A bright living area is viewed through an opening, featuring a ceiling fan and a large window. A comfortable seating arrangement includes a gray sofa, and a coffee table is centered on a plush rug. Green plants add natural elements to the space.
Flat in Wausau
4.98 out of 5 average rating, 228 reviews

Daniel’s Place

Cozy up in this private, one-bedroom, centrally located, upper apartment. (Must walk up a handful of outdoor stairs) Unique, peaceful, and affordable - Daniel’s Place is 3 blocks from the Riverlife walking path, leading directly to downtown, and 3 miles away from Granite Peak Ski Resort. Daniel’s Place is the perfect spot for weekend ski trips, city biking, trying local restaurants, farmers markets, kayaking, and exploring the city of Wausau. Come make yourself at home 🙂

Top guest favourite
A charming wooden cabin nestled among tall pines showcases a welcoming deck with steps leading to the entrance. A flower-filled barrel planter adds a touch of color, while the surrounding natural landscape enhances the serene atmosphere of this secluded retreat.
Cabin in Hancock
4.95 out of 5 average rating, 435 reviews

Peaceful Wooded Sanctuary:A/C and private dog park

Unplug. Unwind. Connect with nature. Come enjoy our 700 sq.ft. cabin on 6 wooded acres. Fish the trout stream, hike, bike, swim! See hummingbirds hover at the feeder, watch for deer or bald eagles. The outdoor recreational opportunities are endless. Listen to the wind whisper while you sway in the hammock. Play in the treehouse! Escape to the peaceful pines and let whippoorwills sing you to sleep at day's end. Bring your pup and enjoy the 1,200 sq. ft. private dog park.

Top guest favourite
A spacious bell tent is nestled among trees, adorned with string lights that create a subtle glow. A comfortable seating area is arranged nearby, inviting relaxation amidst lush greenery. The path leading to the tent is surrounded by dense plants, enhancing the serene camping experience.
Tent in Kendall
4.89 out of 5 average rating, 133 reviews

Driftless Glamping on a Bluff

Rustic camping in the Driftless Region on the top of a bluff in a 20ft. Bell Tent. Relax, without having to pack, set up camp, and tear down and put away when you get home, more time to do things you enjoy. Go trout fishing, walk or ride the Omaha Trail Tunnel, Elroy- Sparta Trail, or the 400 Trail. Necedah Wildlife Refuge, Buckhorn, Castle Rock, Wisconsin Dells, Amish scenic drive, and Wildcat State Park with canoeing down the Kickapoo River are all within 30 minutes.

Top guest favourite
A wooden tray is positioned on a low table, showcasing a welcoming note alongside a dark vase filled with dried grass. The background features a queen-sized bed dressed in neutral linens, complemented by a softly colored wall that adds to the room's serene ambiance.
Guest suite in Wausau
5 out of 5 average rating, 101 reviews

Sylvan Hill Studio by Bike Trails and Tubing Hill

This cozy studio sits on the edge of the quiet Forest Park neighborhood just 2 minutes from Tribute Golf course and Gilbert Park & Boat Launch. It's 7 minutes from Downtown Wausau’s 400 Block with its quaint shops, restaurants and The Grand Theater! Plus, concerts in the summer and ice skating in the winter. Explore Granite Peak Ski Area and Rib Mountain State Park, just 15 minutes away! And both Aspirus and Marshfield medical facilities are within a few miles.

Top guest favourite
A serene bedroom is featured with a large bed dressed in a white coverlet and plush pillows. A dark accent wall enhances the modern decor. Natural light enters through a nearby window, while a round mirror and stylish light fixture add to the room's aesthetic.
Home in Marshfield
5 out of 5 average rating, 139 reviews

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.

Popular amenities for Pittsville holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Wood County
  5. Pittsville