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Compare 42 Vacation Homes in Rollingstone with updated reviews, rates, and availability.

Family friendly in the peaceful heart of town
Kitchen. Ladder can be removed. Everyday needs are easily in reach on shelves.

Family friendly in the peaceful heart of town

10.0 out of 10, Exceptional, (88)
"Beautiful house, close to the lake. Had everything you could need."
Family friendly in the peaceful heart of town
The River Cabin Summ

The River Cabin Summ

10.0 out of 10, Exceptional, (8)
"It was just beautiful!"
The River Cabin Summ
Sunrise on Skyline - Indoor Pool - Arcades - Amazing Views!
You'll have endless fun in our endless pool! Overlooks the Mississippi River!

Sunrise on Skyline - Indoor Pool - Arcades - Amazing Views!

10.0 out of 10, Exceptional, (63)
"The place was wonderful! Pool was very clean and nice! The reason I gave only 4 stars on cleanliness is that the cleaners need to move the furniture and sweep- we cleaned up stuff that wasn’t ours. We would definitely stay again and tell others about this place! The views are so beautiful!!! Thank you so much!!"
Sunrise on Skyline - Indoor Pool - Arcades - Amazing Views!
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
Property grounds

The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs

10.0 out of 10, Exceptional, (41)
"View and spacious rooms and bedrooms! Every couple loved having a bathroom, with family it was fine using the 5th bathroom in another’s bedroom which had the 5th bathroom. Loved the balcony around most of the house. Sister in law locked us out of the house but management was able to solve the issue immediately, what a lifesaver to get a tired family after a wedding into the house. Wish we had more time there to be with bothers and sisters. "
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
Spacious Historic Gem with Modern Features
TV/lounge area of living room.

Spacious Historic Gem with Modern Features

10.0 out of 10, Exceptional, (18)
"Huge house with plenty of room for everyone to sleep. Great old time charm in this place. Huge backyard and plenty of parking and extremely easy to find and access - right on the main drag of the town. Easily walk to great restaurants too!! If you have a large group this is the place for you! "
Spacious Historic Gem with Modern Features
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Welcome to the Village House Inn. Whole house vacation rental.

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (118)
"This property is amazing! By far the best VRBO property I have had the pleasure to stay."
The price is AED 1,286
AED 2,027 total
includes taxes & fees
6 Jan - 7 January 2025
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Entire high-quality lodge well equipped and tranquil - See ALBINO deer!
Exterior

Entire high-quality lodge well equipped and tranquil - See ALBINO deer!

10.0 out of 10, Exceptional, (75)
"Great communication with the owners and the place was extremely clean! I hope I get the chance to stay here again! "
Entire high-quality lodge well equipped and tranquil - See ALBINO deer!
Mississippi River View with updated driveway

Mississippi River View with updated driveway

9.4 out of 10, Exceptional, (126)
"The inside of the house was great!"
Mississippi River View with updated driveway
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
Dining

Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.

10.0 out of 10, Exceptional, (42)
"It is conveniently located; excellent hosts; property is great."
The price is AED 606
AED 729 total
includes taxes & fees
30 Dec - 31 Dec
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
Tamarack Point Homestead
Exterior

Tamarack Point Homestead

10.0 out of 10, Exceptional, (22)
"This is the best VRBO weve ever stayed in. The amenities were amazing . We had a great stay. The owners were very accommodating and responds quickly. Thank you for your excellent service."
The price is AED 353
AED 450 total
includes taxes & fees
30 Dec - 31 Dec
Tamarack Point Homestead
Great River Road - Victorian Historic Home (1898)
Exterior

Great River Road - Victorian Historic Home (1898)

10.0 out of 10, Exceptional, (4)
"Great house for our family group of 12. The kitchens were well stocked for cooking, which we did a lot of. The house was very comfortably furnished. It was easy to gather as a large group in the family room or dining room, but also lots of space to be by one's self. The last morning of our stay, we all ended up in the front room just talking before we left."
The price is AED 1,587
AED 2,538 total
includes taxes & fees
2 Jan - 3 January 2025
Great River Road - Victorian Historic Home (1898)
The Perfect All Seasons Getaway
Property grounds

The Perfect All Seasons Getaway

9.6 out of 10, Exceptional, (24)
"Great stay overall! "
The Perfect All Seasons Getaway
MCR is a property that features seclusion and privacy that is hard to find.

MCR is a property that features seclusion and privacy that is hard to find.

10.0 out of 10, Exceptional, (80)
"Money Creek Ranch is simply amazing. The house and property were absolutely incredible for our family to check out and be out in nature. The house is the most well equipped VRBO we’ve stayed in. Lots for the kids to do in the house, and seemingly endless trails to explore outside. We’ll definitely be back. "
MCR is a property that features seclusion and privacy that is hard to find.
Farmhouse Apartment - Great River Road Historic Home (1898)
Amazing Mississippi River views from the sun-room

Farmhouse Apartment - Great River Road Historic Home (1898)

9.8 out of 10, Exceptional, (11)
"My long time friend and I decided to get away for a few days, it was at last minute idea. We decided to go to Fountain City/Winona area to be by the river and see that part of Wisconsin/Mn. Enjoyed our time to relax and shop. The Farmhouse apartment is very nice and is exactly as described. If you love old charm in a small town, you will enjoy your stay. "
The price is AED 536
AED 904 total
includes taxes & fees
2 Jan - 3 January 2025
Farmhouse Apartment - Great River Road Historic Home (1898)
The Broadway Exchange
Bathroom

The Broadway Exchange

9.8 out of 10, Exceptional, (18)
"Comfy beds. Good gathering spaces…living room, kitchen island, dining room. Outdoor space too. "
The Broadway Exchange
Victorian era Mississippi riverview retreat.
Property grounds

Victorian era Mississippi riverview retreat.

9.6 out of 10, Exceptional, (24)
"The house was perfect for our needs. We had plenty of space for our group. The house was clean and well-stocked with everything we needed. The location was perfect and a block off of Highway 35. We will absolutely consider staying here again!"
Victorian era Mississippi riverview retreat.
The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air
Make yourself at home in this newly updated kitchen

The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air

9.8 out of 10, Exceptional, (28)
"A perfect place to gather after a day of sight seeing. "
The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air
Vintage Lustron Home Piece of History
Room

Vintage Lustron Home Piece of History

10.0 out of 10, Exceptional, (17)
"Our family enjoyed staying in this piece of pre-fab home history. Very clean and comfortable accommodations. Would visit again."
The price is AED 551
AED 844 total
includes taxes & fees
1 Jan - 2 January 2025
Vintage Lustron Home Piece of History
Discover ‘Riverview Radiance,' a 5BR Minneiska marvel where the Mississippi meets modern luxury. Perfect for large groups, this home boasts a fully-equipped kitchen, sprawling views, and a suite of entertainment options. Revel in comfort with plush
Front Entrance

Discover ‘Riverview Radiance,' a 5BR Minneiska marvel where the Mississippi meets modern luxury. Perfect for large groups, this home boasts a fully-equipped kitchen, sprawling views, and a suite of entertainment options. Revel in comfort with plush

10.0 out of 10, Exceptional, (8)
"This was a wonderful place. We would go back again!"
The price is AED 1,675
AED 2,026 total
includes taxes & fees
2 Jan - 3 January 2025
Discover ‘Riverview Radiance,' a 5BR Minneiska marvel where the Mississippi meets modern luxury. Perfect for large groups, this home boasts a fully-equipped kitchen, sprawling views, and a suite of entertainment options. Revel in comfort with plush
Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life
Front of Guest House

Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life

10.0 out of 10, Exceptional, (34)
"We all loved this farm home! It was very nice. We had more than enough room for 7 adults. Checking out the chickens and goats, and all the love from Larry Daniel Tiger (their kitty) was an added plus! Did I mention the fresh eggs for breakfast?! "
Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Rollingstone

Entire cozy Rollingstone apt in Mississippi Valley, just 10 min from Winona!
Living area

Entire cozy Rollingstone apt in Mississippi Valley, just 10 min from Winona!

10.0 out of 10, Exceptional, (12)
"We truly enjoyed our time at Hattie's Place. Beautifully decorated with all the amenities one could hope for. LOVED the coffee and tea options! Great communication with hosts as well. "
Entire cozy Rollingstone apt in Mississippi Valley, just 10 min from Winona!
Treehouse Cabin in the Bluff Woodlands
Exterior in winter

Treehouse Cabin in the Bluff Woodlands

9.6 out of 10, Exceptional, (9)
"Absolutely loved this cabin stay for our family! Clean, quick drive to whitewater state park for day adventures, and so nice to come back and enjoy the time at the cabin. Bathrooms were great and clean! Nice to have running warm water for our toddler along for the trip. Will definitely be considering booking again! :)"
The price is AED 347
AED 603 total
includes taxes & fees
1 Jan - 2 January 2025
Treehouse Cabin in the Bluff Woodlands
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Welcome to the Village House Inn. Whole house vacation rental.

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (118)
"This property is amazing! By far the best VRBO property I have had the pleasure to stay."
The price is AED 1,286
AED 2,027 total
includes taxes & fees
6 Jan - 7 January 2025
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.