Vacation rentals in Winslow

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

GOOSE ISLAND CABIN -Secluded Riverside Eco-Retreat

Nestled along the banks of the Rock River under tall oaks, ye ol cabin was built by early settlers in 1907. Legit rustic charm. Secluded yet only 10 mins from the fun town of Oregon. 100 acres of private property, bordering Lowden-Miller State Forest. Includes use of canoes/kayaks, large riverfront yard, grills, hammocks, deck, porch and firewood. $33/night per person or pet after first 2 people. Message Tim about accomodating larger groups and events. Closed for winter November through March.

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.

Cool, Roomy, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs, included in your reservation, must be leashed when outside.

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

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

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

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.

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.

Cozy Cabin on Decatur Lake

Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!

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.

The Car Wash Inn A Unique Stay

Enjoy a unique stay inside a beautifully revitalized single bay 1950s car wash. Only minutes away from historic downtown Shullsburg. This space has been thoughtfully designed to retain it's industrial charm with a nostalgic ambiance, while offering modern amenities for a comfortable stay. ~20 miles to Galena, IL ~25 miles to Mineral Point, WI ~25 miles to Dubuque, IA ~ATV Trail Access with large parking area