Vacation rentals in Little Chicago

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!

Spacious Upper Barn Sleeps up to 7 Near WI River

Relax & unwind in this peaceful, one-of-a-kind upper barn (not handicap accessible) stay in the Northwoods of Wisconsin. Blending rustic charm with modern comfort, this kid-friendly retreat features an outdoor play area & a whimsical playhouse. The memorable architecture includes a stunning spiral stairway, crafted from trees harvested on our 4.5-acre property, leading up through a reclaimed silo. Every detail at Friedenswald tells a story. (The spiral stairway is not handicap accessible.)

The Prayer Cabin 60 Acres Most Incredible View

This serene cordwood timber-frame cabin perched high on a hill near Timm's Hill is pure magic. The winding driveway bordered by massive stones sets the tone for total tranquility on 60 private acres. Step inside to gorgeous natural woodwork, radiant in floor heat and a cozy loft overlooking the open lower level with jaw dropping views in every direction. Tucked away in the quiet town of Hill, this unique north-woods gem feels worlds away yet right next door to Wisconsin's highest point.

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.

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 🙂

Retreat at 7th Ave.

Let us help you feel right at home in Central Wisconsin! Home includes spacious backyard with deck and outdoor furniture! This home has everything you may need for a family gathering, or weekend on the slopes. 3 bedrooms, 2 bathrooms and a fully equipped kitchen for you to cook in. Driveway & street parking plus WIFI! 6 minutes from Downtown Wausau 6 minutes from shopping and restaurants in Rib Mountains 10 minutes from Granite Peak Ski Area 7 minutes from Aspirus

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!

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!

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.

Porch Light Place - Cozy, Quiet & Comfortable!

Keep it simple at this peaceful, newly renovated and centrally-located home. This cozy small house is close to Granit Peak Ski Area, Marathon Park, Lake Wausau, Rib Mountain Golf Course, Whitewater Kayaking Park, Downtown Wausau's 400 Block, Aspirus Wausau Hospital, many restaurants and so much more. Our home is great for adventurers, couples or business travelers We are **PET FRIENDLY** and looking forward to hosting you!

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.

Game Room, Yard Games, & Bunks By Wisconsin River

Tucked in the trees of Wausau, Cottage on 6th blends modern design with unique architecture. Enjoy a spacious yard with fire pit, BBQ grill, and game room—perfect for relaxing or entertaining. Minutes from Rib Mountain and downtown Wausau’s shops, restaurants, and outdoor fun. Whether you're here to hike, ski, or unwind by the fire, this cottage is your home base for a your next getaway.