Holiday rentals in Rollingstone

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Rollingstone

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Guest favourite
A vibrant sunset casts shades of pink and purple over calm waters, with silhouettes of hills in the background. A group of people is gathered on a wooden dock, with a boat covered in a tarpaulin nearby. Trees frame the scene, adding to the natural beauty.
Cottage in La Crosse
4.87 out of 5 average rating, 378 reviews

Sunsets on the Edge

My place is 10 minutes from downtown La Crosse, close to the airport, but you'll feel a world away. You’ll love my place because of the peace and quiet, but mostly THE VIEWS. All the modern conveniences of dishwasher, microwave, shower and stove/fridge, washer & dryer. You'll never see the same sunset! My place is good for two people or solo adventurers.Full list of amenities available, but worth noting here that coffee is NOT provided. There is a drip coffee maker, as well as a spot for kpods.

Top guest favourite
A dining table is set on a covered wooden patio, featuring a variety of breakfast items, including eggs, fruit, and beverages. Lush greenery and tree canopies create a natural backdrop, while the expansive view offers a glimpse of the landscape stretching toward the horizon.
Cabin in Mindoro
4.97 out of 5 average rating, 268 reviews

Stunning Views! - Bunker Hill @HighPointRetreats

Perched in the solitude of nature, our ridge top cabin offers a picturesque view at one of the top elevations in all La Crosse County. Cozy up to your loved ones, relax with friends, or find inspiration in this luxury cabin in the woods. Bunker Hill sleeps four and is non-smoking. Get your front row sunset seats on the private patio and relax by the fire. Immerse yourself in the tranquility and come stay us. *Check out our six other one-of-a-kind retreats listed on Airbnb located in Mindoro, WI

Guest favourite
A spacious bed with a brass headboard is center-stage in the room, accented by layers of blue and white bedding. Nightstands with lamps are placed on either side, contributing to the overall balanced layout. Soft curtains frame a window, allowing natural light to fill the space.
Home in Minnesota City
4.97 out of 5 average rating, 314 reviews

✨Vintage Lustron Home✨

Enjoy a stay in this vintage Lustron Home. It is a unique home. It has two bedrooms, and a sofa sleeper in the living room. The master bedroom has a queen size bed. The second bedroom has two twin beds. This home offers a washer and dryer for your convenience. It has a large fenced yard to enjoy during your stay. Off street parking and Wi-Fi included. This home is in a very peaceful neighborhood. Located close to Winona State University and St. Mary's University. There are State Parks close also

Top guest favourite
An open kitchen and living space feature a large wooden countertop with three metal stools. The room is illuminated by a stylish chandelier, with a brick accent wall providing character. Large windows allow natural light to fill the area, showcasing the hardwood floors.
Loft in Winona
4.99 out of 5 average rating, 808 reviews

Penthouse Retreat-Near Downtown Winona!

Hi! This beautiful loft is conveniently located in the heart of Winona MN! Only a few blocks from the downtown and in close proximity to many other attractions Winona has to offer such as: Coffee, restaurants, a wine bar, Winona State University, Mississippi River, Lake Winona, hiking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next extended stay in beautiful Winona a memorable one! * MUST CLIMB STAIRS TO UNIT- LOCATED ON THE 3RD LEVEL

Top guest favourite
A cozy living room features a dark blue sofa and a comfortable brown leather armchair. A round coffee table sits on a patterned area rug, surrounded by framed artwork on the walls. Natural light enters through large windows with gray drapes.
Flat in Rollingstone
5 out of 5 average rating, 44 reviews

Entire cozy Rollingstone apt. 10 min to Winona!

In town it's simply known as “Hattie’s”, and she's always been known for her kind smile. Whether you're planning family visits or local adventures, we hope you love staying at Hattie’s. Just 10-mins. from Winona (WSU/St. Mary’s University), Whitewater State Park & Prairie Island, hiking, biking, snowmobiling, hunting, kayaking, boating, fishing & wineries. Hattie's is an entire apt. above once Jung and River’s Mercantile (1850s) combining comfy old and new, with a touch of Luxemburg history.

Top guest favourite
A cozy living room is showcased, featuring a wood-burning stove positioned on a stone base with stacked firewood. A light-colored sofa is seen, with a decorative floor lamp nearby. The walls are painted in neutral tones, enhancing the room's relaxing ambiance.
Cottage in Winona
4.92 out of 5 average rating, 110 reviews

Quiet Cottage in the Valley with Sauna

Nestled in the bluffs of Winona, Minnesota, The Driftless Retreat is a cottage in the valley just one mile from Saint Mary's University and a 10 minute drive to downtown Winona and the Mississippi River. The cottage features a private front and back entrance, large backyard, and woodburning fireplace. Our hope is that The Driftless Retreat is just that, a retreat away from the every day. We believe that every detail matters and take pride in making your time here relaxing and enjoyable.

Top guest favourite
A serene view of the Mississippi River is captured, featuring a boat and a paddleboarder on calm waters. Lush green trees line the riverbanks, while gentle hills rise in the background under a cloudy sky.
Home in Fountain City
4.95 out of 5 average rating, 154 reviews

River Road Abode: breathtaking river views

Entire 2 bedroom home with amazing views of the Mississippi from every room in the house. 3 unique decks to watch birds, barges, boats, bluffs and trains. Out front you can wave at people passing by on the Great River Road. Located near WI and MN state parks, wineries, breweries, and restaurants. Adventure outdoors or stay in and watch all the Mississippi has to offer from the private patio and decks. Trains pass by property day & night. Home is well insulated & ear plugs are provided.

Top guest favourite
A private deck is seen on the upper level, adorned with vibrant flower pots and surrounded by greenery. The view extends towards the Mississippi River and distant bluffs, framed by trees that provide natural shade.
Home in Fountain City
4.97 out of 5 average rating, 191 reviews

Bluffside cottage with gorgeous river views

Hill Street House is the quintessential river-town residence, located within walking distance of Fountain City's quaint downtown, legendary pubs, and riverfront, but just far enough from the highway and trains to still get a good night's sleep. Perched snuggly on the bluffside overlooking the Mississippi River, you'll see an ever-changing panorama of river boats, barges, and birds in flight against a backdrop of Minnesota bluffs in the distance and a jumble of rooftops below.

Top guest favourite
The interior of the silo guesthouse features a circular design with wooden beams overhead. A cozy seating area includes a large sectional sofa and a stylish ottoman. Natural light enters through multiple windows, enhancing the space, while a staircase leads to a loft area.
Farm stay in Caledonia
4.99 out of 5 average rating, 116 reviews

Silo Loft Guesthouse

Our silo guesthouse provides a beautiful country retreat surrounded by hundreds of acres of woods and farm land. This working dairy farm is the perfect stay for a tranquil get away or the full dairy farm experience. If you’re looking for a CLEAN, peaceful & unique stay, this is the place for you! Recent guests say it’s the “hidden gem” of MN! Just 10-30 minutes from local coffee shops, restaurants, and many outdoor activities, this getaway has something for everyone!

Guest favourite
A park model home is positioned on a stone terrace, surrounded by lush greenery. Large windows offer expansive views of the surrounding landscape. A wooden deck with seating is visible, extending the living space outdoors, with a tranquil atmosphere conveyed by the scenic backdrop.
Cabin in De Soto
4.96 out of 5 average rating, 144 reviews

Paradise Point sleeps 2 Hot Tub

1 bedroom 1 bath with loft. Cozy home where you can see Paradise. This memorable place is anything but ordinary. Views for miles of the Mississippi River, bluff tops and you can soar with the Eagles. What a place to relax in the newly added hot tub while you enjoy the view in what is call "God's Country". This is promised to be a one of a kind view. The Deck with comfortable outdoor seating Located in the heart of WIsconsin's Driftless Region.

Guest favourite
The interior of the tiny house features a cozy seating area with two individuals engaged in conversation. A small table is positioned near a well-equipped kitchen area, which includes a stove. Natural light fills the space through large windows, complemented by colorful artwork on the walls.
Tiny home in Winona
4.95 out of 5 average rating, 165 reviews

Potluck String Lodge (PSL)

Potluck String Lodge (PSL) is situated within Prairie Island Campground along the Mississippi River. With cottony sheets, coffee & towels, paddle sport equipment & bikes, and an outdoor fire ring, you can simply show-up, relax, reconnect, and recreate. This tiny house tells a story about the Boats and Bluegrass music festival and one of the campground picking circles hosted by the Potluck String Band.

Top guest favourite
A scenic view displays the homestead surrounded by rolling hills and fields. The vintage white house is complemented by several outbuildings. Autumn colors are highlighted in the trees and grass, with a driveway leading through a yard with lush greenery.
Loft in Arcadia
4.98 out of 5 average rating, 184 reviews

Tamarack Point Homestead

Tamarack Point Homestead is located between Arcadia, WI and Centerville, WI in the beautiful valley of Tamarack. This scenic 150 year old homestead has an outbuilding loft that allows you to enjoy the country lifestyle and experience the best that Trempealeau County has to offer. Certified to operate by the Trempealeau County Health Department.

Popular amenities for Rollingstone holiday rentals

  1. Airbnb
  2. United States
  3. Minnesota
  4. Winona County
  5. Rollingstone