Holiday rentals in Winslow

D&D Coastal Farmhouse Apartment Not near any water

This building was built in the late 1890's and was the main grocery store in South Wayne, WI. For years it was used as storage until Dan and Deb renovated it over the last year into this beautiful space! Plenty of parking and great food options within 1 block make D&D Coastal Farmhouse Airbnb a great choice for your stay in Southwest Wisconsin. Main Hubs within 45 minutes: Dubuque, Madison, New Glarus, and Rockford Not handicap accessible. Must Be able to climb stairs. Off street parking.

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.

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.

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

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

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

Pool Table + Ping Pong | Fireplaces | Hot Tub

Escape to this spacious 4-bedroom, 5-bath luxury retreat in the Apple Canyon Lake community—perfect for relaxing, reconnecting, and enjoying time together with beautiful lake views and incredible gathering spaces throughout the home. ✨ HIGHLIGHTS • Stunning wraparound stone fireplace 🔥 • Basement game room with pool table, ping pong, foosball + darts 🎯 • Huge wall of windows + soaring ceilings • Large Smart TVs + fast WiFi • Minutes to golf + dining ⛳ • 12pm check-in & check-out

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

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

Howardsville Schoolhouse

This lovingly restored schoolhouse blends history with modern comfort. Set in a peaceful rural location, it features an open living area, fully equipped kitchen with seating for 12, and cozy sitting area with fireplace and play area. Enjoy a spa-like bath with clawfoot tub, king bedroom, and laundry. A perfect mix of new, refurbished, and antique details create a unique, inviting retreat.

Still Point Tiny House - (Zero Added Cleaning Fee)

Come stay in a real tiny house with a super comfy memory foam full-size bed, sitting/dining area, and its own kitchenette. Think of this as the ultimate "glamping" experience. A private bathroom with an oversized shower is just a few steps across your private brick patio in the adjacent studio building. Great for couples or solo adventurers.