Holiday rentals in Little Chicago

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Top-rated holiday rentals in Little Chicago

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

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Top guest favourite
Cabin in Ogema
4.92 out of 5 average rating, 38 reviews

The Prayer Cabin 60 Acres Most Incredible View

Handcrafted to perfection, this sanctuary features cordwood timber-frame construction, a soaring cathedral ceiling, and a cozy loft. Your experience begins with stunning interior craftsmanship that continues to a rock wall that beautifully hugs the surrounding landscape. The scenery continues endlessly, starting with the sunrise, then sunset, and topped off with stars. You'll be at a loss for words for your review, but one thing you'll know for certain is—when can you book your next stay?I 88k⁹

Top guest favourite
A calm lake view is captured from the dock, featuring clear blue water reflecting the bright sky. Lush trees line the opposite shore, creating a serene backdrop for outdoor activities.
Home in Merrill
4.99 out of 5 average rating, 217 reviews

Big Bear’s Den - On Lake Alexander

This spacious home is located on beautiful Lake Alexander just west of Merrill, Wisconsin. Enjoy the tranquil view year-round as you plan the many activities that this location offers. You bring the boat, and we'll supply the dock. Throw in your ski's or wakeboard, and don't forget your fishing poles! Three pound small mouth bass are not uncommon and the monster's of fresh water fish, the musky, are plentiful. Add in walleyes, crappies, northern pike and this location is a fisherman's dream!

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, 305 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 🙂

Guest favourite
A serene view of vibrant fall foliage frames a tranquil lake scene. Trees with hues of orange, yellow, and green create a picturesque backdrop. A grassy area leads toward the water, enhancing the natural setting.
Home in Wausau
4.97 out of 5 average rating, 111 reviews

Bliss on the Lake

This quiet, 4 bedroom lake house is not only on the water, but a short, five minute drive to Rib Mountain Skiing, a three minute drive to a boat launch, as well as everything Rib Mountain has to offer; shopping, restaurants, night life, and various outdoor activities. It has everything you need to make your holiday warm, comfortable and full of bliss! Cleaning fee credited for all stays 7 days or longer. We can also set up the basement living room area to be a work space.

Top guest favourite
A clean kitchen space features light grey walls and white cabinetry. A wooden table is positioned at the center, adorned with a vase of fresh flowers. Shelves display various decorative items, while a gas stove and sink are visible against the backdrop of a bright window.
Home in Wausau
5.0 out of 5 average rating, 109 reviews

Higgins' Homestead

Experience a quiet, relaxing stay at in a charming little home! Only 1 mile from downtown Wausau, WI. with easy access to restaurants, local YMCA, coffee shops and more! Renovated 3 bed, 1 bath with A/C and elegant maple hardwood floors. Fully equiped kitchen and laundry area, as well as a pleasant fire pit surrounded by strawberries! Queen sized beds in two bedrooms, and a futon in the third. We provide all that you need, to just show up and enjoy a relaxing stay!

Guest favourite
The 1941 WWII Douglas DC-3 Airliner is positioned among trees, elevated on stilts. Soft lights illuminate the wings and tail. The surroundings feature a natural landscape with ferns and foliage, enhancing the setting. The sky shows a gradient of dusk colors, creating a serene ambiance.
Plane in Deerbrook
4.86 out of 5 average rating, 109 reviews

Stay in a piece of History! 1941 WWII Douglas DC-3

1941 WWII Douglas DC-3 Airliner. Flown by the United States Marines for military transport services between Guam, Midway, and Pearl Harbor. Retrofit for overnight comfort with A/C, heat, bathroom, shower, kitchen with outside deck and grilling area, and campfire pit set amongst the trees alongside a private lake with dock. Sleeps four comfortably. Sit in the fully restored, lit cockpit, and feel what it was like to fly one of the most iconic aircraft ever built!

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
5.0 out of 5 average rating, 128 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.

Guest favourite
Home in Wausau
5.0 out of 5 average rating, 9 reviews

Peaceful Secluded Wausau Retreat

Escape to this cozy countryside retreat just outside Wausau, where comfort and convenience meet scenic beauty. This charming home offers a relaxing getaway with plenty of space to unwind, featuring inviting living areas, a fully equipped kitchen, and comfortable bedrooms for a restful stay. The private yard is a true highlight — perfect for morning coffee, evening stargazing under Wisconsin’s clear skies, or a friendly game on the basketball hoop.

Guest favourite
The living area features a cozy brown sectional sofa with an ottoman and an accent chair. A colorful area rug is positioned on the light wood flooring. Natural light enters through large windows, and wall art adds character to the space.
Home in Wausau
4.91 out of 5 average rating, 117 reviews

Cozy home on a quiet street

PRIVATE COZY HOME WITH SPACIOUS KITCHEN AND LIVING NOON Checkout with WASHER & DRYER in house. Fantastic Location: Just a distance to downtown Wausau, where you’ll find coffee shops, theaters, Art Museum, brewery, and a variety of restaurants. Only a 8-minute drive to Schofield and 20 minutes to skiing at Granite Peak. Comfortable & Cozy: Enjoy a bright, inviting atmosphere with room for games and relaxation.

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
5.0 out of 5 average rating, 149 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.

Top guest favourite
An inviting interior features wooden walls that highlight natural textures. A comfortable seating area includes a recliner and side table. A spiral staircase leads to the loft. Large windows offer a view of the surrounding woods, and a patterned rug adds color to the warm tones.
Cabin in Athens
5.0 out of 5 average rating, 110 reviews

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.

Guest favourite
The exterior of the house features a symmetrical facade with a gabled roof and a welcoming porch. White columns support the porch roof, while steps lead up to a blue front door, framed by sidelights. A well-maintained yard with shrubs complements the property.
Home in Wausau
4.87 out of 5 average rating, 116 reviews

The Fairmount

This special property is equipped with a spacious kitchen and dedicated dining area to cook and eat fine meals with your family and friends! It's situated in a quiet neighborhood and close by to the beautiful Memorial Park. Your friends and family will love the cozy feel of this beautiful home! 13 minutes from Granite Peak Ski Hill 6 minutes from Downtown Wausau 12 minutes from Aspirus

Popular amenities for Little Chicago holiday rentals