Holiday rentals in Winslow

Relaxing 3 Bedroom Cabin with Hot Tub and Scenery

Tucked away in the rolling hills of Southern Wisconsin sits a little log home ready for your arrival. Hand built by the caretaker and his family; the Braezel Branch Retreat is named after the stream that runs through the valley. Relax with the whole family in this two-bedroom, two-bathroom cabin with a comfortable open floor plan. Wander through the beautiful walking trails and enjoy the view of the valley from the large front porch. There is also local tubing, kayaking, golfing and wineries.

Location · Value · Comfort

Buck Moon, ATV trail and goats!

Buck Moon is my newly renovated retreat. Designed as a family retreat, nestled into our family farm, I wanted to share this special place with guests. A perfect place to unwind and get away from the city! Catch the sunrise or the sunset from the hammock, take in the starry night sky from the cozy patio, or get a great dose of laughter from playing with my goat kids! Located on an ATV trail road, you have quick access to all the fun adventures of touring the rolling hills of Lafayette County!

Family · Location · Parks

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.

Value · Location · Comfort

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

Family · Location · Outdoor spaces

Family Fall! Hot Tub•Fire In/Out•Game Room•3 Kings

Relax, unwind, & explore at this Fall Retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and fall/winter adventure!

Value · Family · Comfort

Rustic Barn Loft at Oak Springs Farm

Unplug in our gorgeous barn loft above our working barn. Sleep to the sound of crickets and frogs in the pond, then wake up and pet the sheep, goats, rabbits, cats, ducks & chickens. Open floor plan, cathedral ceiling, farm decor, fire pole, sliding barn doors. Full kitchen, jetted tub, rain shower, laundry. Stone patio, fire pit. 2 bedrooms, sleeper sofa, air mattresses. Juice, coffee, and fresh eggs provided when the hens are laying. NO A/C. ABSOLUTELY NO PETS Facebook oakspringsfarmwi

Location · Value · Parking

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Family · Value · Nearby

Hamilton Goebel House

This house is a historic home that was built in 1833 on land owned by Jamison Hamilton, the founder of Darlington. It is not known if he actually lived in the house,but could be assumed. During your stay you will find bits of history and pictures that have been gathered along the way.It has all the comforts of home. A beautiful four bedroom home that has been completely renovated to reflect the old and new times. This home was on the list to be torn down by the city.

Location · Value · Cleanliness

MJ's Penthouse ( A piece of paradise in Monroe)

A beautiful 2000 square foot second floor Penthouse that offers an excellent view of the historic court house and square. Our location gives you walking distance to all places on the square including the 2nd oldest brewery in the country, boutiques, hair and nail salons, home decor , antique shops, clothing and apparel, specialty treats, restaurants and bars. We have free parking out front on the square and also a private elevator for our guests special needs.

Location · Value · Sleep quality

The Old Farmhouse

The old farmhouse is located on a quiet, dead-end road. It sits on top of a picturesque hill surrounded by rolling farmland. The Pecatonica river surrounds the farm on three sides. The farmhouse is the perfect place for quiet time and relaxation. The Farmhouse was built in 1914. It still has the original woodwork, and beautiful hardwood floors. Sit on the porch or sit around the fire pit and enjoy the beautiful fall foliage.

Family · Location · Checkout

The Dairy at the Wegmueller Farm

Welcome! You are about to experience life on an active 4th-generation farm nestled in the rolling hills of Green County. Meet the cows, feed the pigs, befriend a horse, or just enjoy the relaxing and peaceful serenity of rural Wisconsin farm life. Located less than five miles from Monroe, this home away from home is close enough to all that Monroe & the surrounding community has to offer, but still has room to stretch your legs.

Location · Value · Wifi

Welcome to the "Bat Cave"!

Completely renovated 3 bedroom, 2 bathroom home with walk in basement allowing easy access for ATV and snowmobile enthusiasts. Direct access to the Cheese Country trail and one block from The Vault and Cash's bar and grill! Amenities include washer and dryer, wifi, 3 smart TV's and a unique gathering spot with poker table in the basement.

Location · Family · Check-in