Holiday houses in Rollingstone

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Top-rated holiday rentals in Rollingstone

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Guest favourite
A charming treehouse is nestled among the lush branches of a large, mature oak tree. The wooden structure features multiple levels with a spacious deck that connects to the main entrance, surrounded by greenery, creating a serene and natural environment.
Home in Cottage Grove
4.98 out of 5 average rating, 697 reviews

Tree House Luxury Stay

Perched high in the majestic arms of a 150 year old Burr White Oak tree. This cozy 1200 square foot, seven-room house not only has breathtaking views it also has enchanting and delightful surprises befitting of a fairytale. Climb 40 feet up onto the Observation Tower, where a telescope waits for you, ready to scan the night sky, and reveal the panorama of the heavens -- overlooking 500 acres of natural splendor right next door. Step into the hot, bubbling jets of the jacuzzi, or warm caress of the rain shower, and restore your spirits by soothing your muscles, melting away any residual tensions of the day. Get a restful sleep in one of our soft beds. In the morning, pad around on in-floor radiant heated floors (so cozy during winter-time.) Or enjoy your morning coffee on one of four outside decks. And don’t forget to solve the mystery of the Treehouse, that awaits your discovery within its wood beamed walls. This treehouse was custom designed by its architect with three dimensional chess in mind. Artisan architectural details are found throughout. Crystal chandeliers bedeck its high ceilings, and marble countertops grace the elegant, fully appointed kitchen. (A surround sound system helps set the mood for those special dinners in the dining nook.) One of two fireplaces adds luxurious touches to the primary bedroom with a queen bed, and hideaway bed in the secret room, along with a jacuzzi and rain shower in the primary bath, as well as a second bathroom in the secret room. Perfect for honeymooners, couples, business/corporate overnights, solo travelers and families with children over twelve years old. These are only a few of the many luxury details in this spectacular vacation spot must-see. Spend your days snuggled up beside the fireplace of your choice, while enjoying the panoramic views. You can stream your favorite movies and shows with Broadband Wi-Fi throughout the house. Come down for a leisurely walk around the grounds, and stop by to visit and feed the goats and chickens that call Hope Glen Farm their home in the corral of this historic farmstead. Bring your stress levels down and your heart rate up by walking over to Washington County Cottage Grove Park Reserve, just steps away, and answer its call to explore over 550 acres of fields and forests. Go hiking and biking down its trails, geocaching the hills and ravines for hidden treasures, or spend the afternoon fishing and kayaking in the lakes. And don’t let cooler temperatures keep you from discovering the pristine natural beauty of winter! Winter activities include cross country skiing and snowshoeing on the blankets of snow. Breathe deeply of the crisp Minnesota winter air -- truly one of life’s great pleasures. Plus, only a ten minute drive brings you to nearby Afton Alps in Afton State Park offering downhill skiing and snowboarding. For clarity, the Treehouse has 2 private bedrooms: Bedroom 1 is has a queen bed. Bedroom 2 has a bedroom with standard sofa bed with attached half bathroom, which is the secret room a must find. Give yourself the gift of this luxurious enchanting TreeHouse Suite in the treetops, for a enchanting vacation experience you'll never forget. Something to write home about!

Top Guest favourite
A modern tiny house is set within a lush green yard, featuring wooden siding and a metal roof. Large windows provide views of surrounding trees and landscaping. Decorative stones and plants enhance the outdoor space, while a wooden deck offers an entryway to the home.
Tiny home in Black River Falls
4.97 out of 5 average rating, 444 reviews

Tiny on the River

According to Forbes, Escape makes "the most beautiful tiny houses in the world". Ours is perched near our home above the Black River. It's a quiet neighborhood just minutes from the interstate, parks, trails, and our vibrant downtown with cafés, shops, and great restaurants. Enjoy privacy and breathtaking views from the enormous windows or the cozy daybed on the porch! Deer, beaver, eagles, and more make frequent cameos as the seasons paint shifting riverscapes and astonishing sunsets. *No Pets

Top 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
4.98 out of 5 average rating, 305 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
Apartment in Winona
4.95 out of 5 average rating, 262 reviews

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * NO cleaning fee/deposit required * Spacious bedroom with queen size bed, couch and workspace * Fully kitchen with oven, refrigerator, microwave + coffee/tea station * TV, board games and books * All amenities needed for a comfortable stay * Walking distance to WSU and Cotter * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.

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
4.88 out of 5 average rating, 344 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 couples, 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 Keurig for pods.

Top Guest favourite
A spacious dining area features a large black table surrounded by six teal chairs, placed on a striped rug. A vibrant window seat adds color, while a chandelier hangs above, contributing to the room's inviting ambiance. The kitchen can be seen in the background.
Bungalow in Winona
4.99 out of 5 average rating, 248 reviews

*Prairie Island Bungalow with Water Access*

Welcome to Prairie Island Bungalow (PIB)! Located on Prairie Island in Winona, this home provides the perfect, quiet getaway for work or play, and is your gateway to outdoor adventure in the Winona area. River access is available on our private dock next door! With thoughtful amenities including a fully-stocked kitchen (with coffee and tea!), plush linens, Smart TVs, games and books, a fire pit, snowshoes, and kayak and canoe rentals; we invite you to simply show up and enjoy your stay at PIB!

Top Guest favourite
The cozy kitchen and dining area features light-colored cabinetry and a large countertop. A round table with four red chairs is positioned beneath a wall art piece. Warm wooden paneling lines the walls, complementing the inviting atmosphere.
Farm stay in Dakota
4.94 out of 5 average rating, 299 reviews

The Bungalow at the Healing Refuge

Welcome to The Healing Refuge! Come experience life on a Minnesota farm nestled in the rolling hills of the Driftless region. Relax out on the deck, swing in a hammock among the trees, or enjoy a walk through our beautiful cover crop fields. This is a working farm and depending on the season, you are welcome to help collect eggs, learn from the horses, observe the farm animals, and find out about regenerative agriculture. We want your experience at our farm to be relaxing and refreshing!

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, 143 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.

Guest favourite
A cozy cabin interior features natural wood paneling throughout. A spacious bed is positioned near a window with views of the surrounding greenery. A leather couch and a rocking chair add to the seating options, complemented by a small table.
Tiny home in Plainview
4.95 out of 5 average rating, 155 reviews

Quaint 1 bedroom cabin, with amazing views!

Peaceful 1 bedroom cabin overlooking views of the beautiful whitewater valley (35 minutes away from Rochester Minnesota). Perfect for a quiet, off-the-grid, retreat. - compost toilet -two burner stove -gas heater for the colder months -5 gallons of water included, more If needed Queen size bed beneath 3ft by 3ft skylight with stunning views of stars at night. 120 private acres connected on two sides by the (WMA). 1 + mile of personal private hiking trails with scenic views.

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, 157 reviews

Bluffside cottage with gorgeous 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
A modern cabin is situated on a grassy plot, surrounded by trees displaying autumn colors. The structure features a dark roof and a wooden door, with patio seating visible on the deck. The landscape includes gentle hills and a clear sky.
Cabin in Lanesboro
5 out of 5 average rating, 112 reviews

Trout Creek Cabin

The cabin sits in a valley on the South Fork of the Root River. Fire pit, hot tub and 2 large patios both with outdoor dining, steps away from the trout stream make this unique property a peaceful, romantic get away. A short drive from the Root River bike trail and Lanesboro making it easy to take advantage of the best historic bluff country has to offer.

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
4.99 out of 5 average rating, 172 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