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Compare 53 Vacation Homes in Rollingstone with updated reviews, rates, and availability.

Tamarack Point Homestead

10.0 out of 10, Exceptional, (25)
"First time staying here loved it, sleep great beautiful property loft was very clean and well set up. I have already booked another stay. Wonderful Host."
Tamarack Point Homestead

Bluffside cottage with gorgeous river views

10.0 out of 10, Exceptional, (27)
"So cute/quiet/clean with gorgeous views of the river!"
Bluffside cottage with gorgeous river views

Family friendly in the peaceful heart of town

10.0 out of 10, Exceptional, (92)
"We had a lovely and comfortable stay for Thanksgiving. Walkable or very short drive to the sights and amenities of Winona! "
Family friendly in the peaceful heart of town

Vintage Lustron Home Piece of History

10.0 out of 10, Exceptional, (20)
"We've stayed here several times and enjoy it every time. We enjoy visiting the area and exploring what it has to offer while visiting friends"
The price is SAR 563
SAR 868 total
includes taxes & fees
2 Jun - 3 Jun
Vintage Lustron Home Piece of History

Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

10.0 out of 10, Exceptional, (14)
"Very clean and comfortable. "
The price is SAR 975
SAR 1,199 total
includes taxes & fees
4 Jun - 5 Jun
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

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

10.0 out of 10, Exceptional, (69)
"Perfect for a family get away. Kids loved the pool. "
Sunrise on Skyline - Indoor Pool - Arcades - Amazing Views!

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

10.0 out of 10, Exceptional, (7)
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs

10.0 out of 10, Exceptional, (46)
"Lots of beds and bathrooms to share the weekend with extended family."
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (124)
"This property is amazing! By far the best VRBO property I have had the pleasure to stay."
The price is SAR 1,200
SAR 1,938 total
includes taxes & fees
9 Jun - 10 Jun
Charming Brick Farmhouse with a Touch of Elegance. -Winona

Victorian era Mississippi riverview retreat.

9.8 out of 10, Exceptional, (28)
"Property was clean, comfortable, and just what we were looking for."
Victorian era Mississippi riverview retreat.

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

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

10.0 out of 10, Exceptional, (80)
"This place is absolutely gorgeous! Very accommodating, fun little surrounding towns and tons of trails! Highly recommend for large families! The layout has great space!"
MCR is a property that features seclusion and privacy that is hard to find.

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

10.0 out of 10, Exceptional, (76)
"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!

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

10.0 out of 10, Exceptional, (40)
"This home was an incredible place to lay our heads after active days on the ice. It was clean, comfortable, the host was kind and considerate."
Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life

Spacious Historic Gem with Modern Features

10.0 out of 10, Exceptional, (22)
"Rented this place for weekend of Grumpy Old Man festival. Perfect location to walk to all events. House was comfortable. Check in/ check out easy. Owner was organized and communicated well. Lots of seating to accommodate our party. Only downfalls were limited hot water while showering and the blue bedroom was chilly compared to other rooms. Would definitely stay there again. "
Spacious Historic Gem with Modern Features

Buffalo City Cabin

9.6 out of 10, Exceptional, (37)
"The property met our expectations. It was small but comfortable in a quiet neighborhood within walking distance to 2 bars/restaurants and a convenience store. Centrally located between a couple of our favorite wineries and cool river towns."
Buffalo City Cabin

Family-Friendly 3-bedroom house, Firepit, Clawfoot Tub, Local Attractions

Family-Friendly 3-bedroom house, Firepit, Clawfoot Tub, Local Attractions

Riverfront 4-Bedroom Home in Wabasha

Riverfront 4-Bedroom Home in Wabasha

Mississippi River View with updated driveway

9.6 out of 10, Exceptional, (127)
"The inside of the house was great!"
Mississippi River View with updated driveway

The Broadway Exchange

10.0 out of 10, Exceptional, (27)
"The owners are very timely in their communication. The home is always clean and has things to do (books, games) and information about what is going on around town. While my kids all have their own space, the house lends itself to hanging out and enjoying each other's company! I love that house is updated, but still retains some original craftmanship and charm."
The Broadway Exchange
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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