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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 43 Vacation Homes in Rollingstone with updated reviews, rates, and availability.

Bluffside cottage with gorgeous river views
View of Mississippi River from upper deck

Bluffside cottage with gorgeous river views

10.0 out of 10, Exceptional, (21)
"So cute/quiet/clean with gorgeous views of the river!"
Bluffside cottage with gorgeous river views
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, (120)
"Our family stayed at the Village House Inn over Christmas and it was perfect for accommodating a large group very comfortably. The location and proximity to Winona was also ideal. We will definitely be back! "
The price is SAR 1,069
SAR 1,764 total
includes taxes & fees
18 Feb - 19 Feb
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Exterior

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

10.0 out of 10, Exceptional, (12)
"the inside was beautiful. the neighborhood was decent and quiet. very comfortable stay!"
The price is SAR 881
SAR 1,079 total
includes taxes & fees
18 Feb - 19 Feb
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
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, (65)
"The views are absolutely breathtaking! And the house itself, was more beautiful than the pictures could ever capture! The amenities were awesome and kept us busy! Definitely a 5 out of 5!! "
Sunrise on Skyline - Indoor Pool - Arcades - Amazing Views!
The River Cabin Summ
Nice size living room with amazing views of the Mississippi River

The River Cabin Summ

10.0 out of 10, Exceptional, (8)
"It was just beautiful!"
The River Cabin Summ
Tamarack Point Homestead
Exterior

Tamarack Point Homestead

10.0 out of 10, Exceptional, (23)
"Lovely property, super clean, and so many nice, unexpected amenities!"
The price is SAR 360
SAR 459 total
includes taxes & fees
18 Feb - 19 Feb
Tamarack Point Homestead
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, (43)
"Great place for our ice fishing trip to the Mississippi River. Can’t beat this lodge in terms of meeting our needs and location. Owners are very responsive when questions came up. Would highly recommend. "
The price is SAR 619
SAR 732 total
includes taxes & fees
18 Feb - 19 Feb
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
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
The Broadway Exchange
Bathroom

The Broadway Exchange

10.0 out of 10, Exceptional, (21)
"There's a group of 5 WSU Alumni that get together each year at the end of January. Got tired of the local hotel options so we tried VRBO instead. "
The Broadway Exchange
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!
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, (43)
"The house is perfect for a getaway with friends or family. It is very spacious with a large area for gathering to play games or just visit. The beds are very comfortable with nice linens. We were in town for a Bonspiel at the Centerville Curling Club. Wish we had more time to spend at the house. Make sure to check out The Station - Ma’s Kitchen in town for breakfast and coffee! SO GOOD!"
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
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
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 SAR 1,823
SAR 2,873 total
includes taxes & fees
24 Feb - 25 Feb
Great River Road - Victorian Historic Home (1898)
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 SAR 1,111
SAR 1,358 total
includes taxes & fees
18 Feb - 19 Feb
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
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
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.
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
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
Victorian era Mississippi riverview retreat.
Property grounds

Victorian era Mississippi riverview retreat.

9.6 out of 10, Exceptional, (25)
"Nice clean house. Plenty of room "
Victorian era Mississippi riverview retreat.
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 SAR 547
SAR 925 total
includes taxes & fees
19 Feb - 20 Feb
Farmhouse Apartment - Great River Road Historic Home (1898)
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!
Big River Escape Riverside Cabins
Front of property

Big River Escape Riverside Cabins

3.0 star property
9.0 out of 10, Wonderful, (26)
"Quiet comfortable "
The price is SAR 423
SAR 446 total
includes taxes & fees
18 Feb - 19 Feb
Big River Escape Riverside Cabins
Heritage hideaway-Secluded Log Cabin
Property grounds

Heritage hideaway-Secluded Log Cabin

10.0 out of 10, Exceptional, (363)
"This cabin is totally adorable! Perfect for a quiet getaway. Secluded and such a great view! Beautiful drive to neighboring towns. Would love to stay here again in the summer! "
Heritage hideaway-Secluded Log Cabin
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.