Holiday rentals in Livingston

Chestnut Cottage

Built in 1890, Chestnut Cottage is located in the heart of the historic district within easy walking distance of shops, galleries, restaurants and historic sites. The Cottage features a comfortable living room, bright dining room, country kitchen, first floor bathroom and two upstairs bedrooms with one queen bed and one twin bed. Chestnut Cottage features artwork by prominent local artists. Wi-Fi, cable TV, DVD/CD players are included. Complimentary coffee/tea service. Minimum two night stay.

Tree Bear Cabin, on a 67 acre Tree Farm

Step away from the demands of life into this hidden gem. Tree Bear Cabin is a 100% real wood log cabin above the bustle of town, nestled among a 67-acre tree farm. Enjoy the quiet of the forest, and the cozy cabin interior. Play games on the wide lawn, explore the trails throughout the property, and make the most of your trip with our noon check-in time and 4 pm check-out times! Activities close by include fishing, kayaking, hiking, wine tasting, UTV Tours, and visiting local shops & Orchards!

Pale Blue Dot

Live your best life at this colorful oasis. the Pale Blue Dot (aka Earth) that's here -- that's home -- that's us. The world is not just a place you live in, but a playground ready for you to conquer. Treat yourself, kids, pets, to nearby biking/walking trails, new Platteville Inclusive Playground or meander downtown to a quaint coffee shop. We welcome UW-Platteville sports enthusiasts, scholars, parents and friends. "The World is Yours" you ask? It's not just a catchphrase, it's a lifestyle.

Silver Birch Retreat

Relax with the family at this peaceful retreat OR grab your friends for an adventurous getaway. Silver Birch is located just outside the charming Village of Livingston in the beautiful Driftless region of Southwest Wisconsin. Float in your kayak at Blackhawk Lake, go fishing at Governor Dodge, or maybe you want to bring your bicycle to hop on the Military Ridge Trail. Let Silver Birch welcome you home from your adventure or just sit on the deck and watch the windmills turn. *No Cleaning Fees*

Cool quiet country cabin on boulders and 120 acres

Funky, tidy 23 year old country cabin on 120 acres of farmland & woods in a private, quiet rural setting. It's cozy, 950 sq ft, built with stone and wood. Open concept with a two story fireplace, porch fireplace, firepit, and open loft for sleeping (1 bed), with spiral stairs, lots of windows, walnut floors and trim, oak beams and pine kitchen tops. Shower is big and open, with doors opening to a back deck for outdoor showering. Beautiful covered porch overlooking rolling meadows and woods.

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Romantic one bedroom cabin with indoor fireplace

Relax and unwind at this getaway on a private 8 acres. Quaint decor yet newly updated amenities in this cabin only 7 miles away from the historic and charming Galena, Illinois. Convenient access to renowned fine dining and shopping in Galena and Dubuque and surrounding tri-state area, casinos, river life with boating and fishing, museums, cafes, vineyards/wineries, located on ATV/UTV trails and much more. You will find a guidebook in the cabin outlining these attractions and many more.

Tiny House @ Red Barn Farm - Private, Free Parking

Rustica Retreat is a unique tiny house, designed by my husband and I, that maximizes the limited space we have. At 256 square feet, Rustica sounds small, but feels spacious. With 10-foot high vaulted ceiling, as well as six windows that bring the outside, in. Rustica fits her name, with a country chic feel to her. The inside has clean lines, white shiplap walls, wood accented ceiling and counters, and metal accents. Located at Red Barn Farm, a micro fresh cut flower farm in SW WI.

Custom Floating Suite-HOT TUB!

Enjoy a stay directly on the backwaters of the Mississippi River. This custom cabin is floating right on the water, and you won't find anything like it! Grab your loved one or friend and surround yourself in nature, while soaking in the hot tub on the floating patio, or in the beautiful tub inside. Relax in the king size bed thats in front of one of the two fireplaces. The cabin has everything you need, including a small kitchen. This floating oasis is located at Millennium Marina.

Riverside Chalet, LLC.

Welcome to the Wisconsin River! Our 1750 sq. ft. cozy riverside chalet features 300 feet of river frontage, master bedroom in the loft, deck overlooking the river, bunk beds, full kitchen, propane fireplace, firepit, and a natural spring running through the yard. The property offers stunning views from every room in the house as well as easy access to the river. Our location has a beautiful view, stunning in fact, but we are very close to Hwy. 60 and there is heavy traffic noise.

Unplug and get back to nature

The log cabin was built as a place to unwind, relax, and truly unplug. Nestled among 15 acres of rolling hills, the cabin can serve as a place to hunker down and read three novels, or a home base for hiking, cycling and putting the nature back in your life. Be advised, there is NO television and that’s for good reason. Cook, drink, eat, play, relax and refresh yourself. Wake up to the songs of birds and listen to the owls at night while you’re warming yourself around a bonfire.

Deer Trail Cabin

🌿 Cozy cabin tucked in the quiet Wisconsin woods—your perfect spring retreat. Enjoy fresh air, blooming trees, and peaceful forest trails right outside your door. Relax in the outdoor hot tub under the stars, gather around the fire pit in the evening (bring your own wood or collect from the property), and watch the free-range goats and chickens roaming the property. A peaceful, private getaway for couples, small families, or anyone looking to unwind in nature. 🌿