Yn Travel - Vacation Rentals in Historic Downtown Winona

Creekside Cabin Getaway From US $151
         

9.4 (115 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Charming Home 3 Blocks to Winona State University From US $243
         

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10.0 (1 Review)
House
  • Parking
  • Accessibility
  • Security/Safety
Big River Escape Parkside Bungalow From US $230
         

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10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Family friendly in the peaceful heart of town From US $197
         

10.0 (112 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Broadway Exchange From US $261
         

10.0 (32 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
The Exchange 14 | Historic Bldg, Studio, Dwntwn From US $172
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Historic Downtown Winona

Over 40+ Luxury Places to Stay in or Near Historic Downtown Winona
Renovated Mid-Century Modern House From US $484
         

10.0 (58 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
1 Mi to Downtown Welcoming Winona Duplex From US $295
         

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New
Apartment
  • Parking
  • Accessibility
  • Security/Safety
Parkside Pet Friendly Bungalow From US $273
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Cottage by Lake Winona From US $272
         

9.6 (58 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
3 Bed Downtown Apt with Historic Charm & Character From US $260
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
The Exchange 16 | Historic Bldg, Studio, Dwntwn From US $236
         

9.6 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Charming Home: 3 Blocks to Winona State University From US $211
         

Top-Rated Vacation Rentals with a Pool in Historic Downtown Winona

Over 8+ Top-Rated Vacation Rentals with a Pool in or Near Historic Downtown Winona
Fairfield Inn & Suites by Marriott Winona From US $135
         

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9.4 (367 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express & Suites Winona by IHG From US $116
         

9.2 (912 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
AmericInn by Wyndham Winona From US $140
         

9.0 (923 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Plaza Hotel & Suites Winona From US $140
         

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8.8 (1005 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Winona by IHG From US $172
         

8.8 (171 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Express Suites Riverport Inn & Suites From US $112
         

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8.6 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
AmericInn by Wyndham Winona From US $139
         

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8.4 (137 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Fairfield Inn & Suites Winona From US $167
         

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8.1 (82 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Historic Downtown Winona

Over 3+ Pet-Friendly Vacation Rentals in or Near Historic Downtown Winona
Lake Boulevard House From US $103
         

9.4 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Days Inn by Wyndham Winona From US $147
         

6.9 (219 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Super 8 by Wyndham Winona MN From US $100
         

6.8 (248 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Historic Downtown Winona

Over 1+ Large Vacation Homes & Villas in or Near Historic Downtown Winona
Alexander Mansion Bed & Breakfast From US $119
         

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9.7 (186 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View

Wheelchair Accessible Vacation Homes in Historic Downtown Winona

Over 3+ Wheelchair Accessible Vacation Homes in or Near Historic Downtown Winona
The Exchange 24 | Historic Bldg, Studio, Dwntwn From US $148
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
The Exchange 23 | Historic Bldg, 1 BR, Dwntwn From US $208
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Private Room in Dorm-Style Building From US $43
         

New
House
  • Air Conditioner
  • Wheelchair Accessible
  • Bedding/Linens

Historic Downtown Winona Vacation Rentals and Airbnb Places to Stay Under $200

Over 12+ Historic Downtown Winona Vacation Rentals and Airbnb Places to Stay Under $200
The Exchange 11 | Historic Bldg, 1 BR, Dwntwn From US $171
         

9.8 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Carriage House Bed & Breakfast From US $152
         

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9.4 (75 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Alexander Mansion Bed and Breakfast From US $141
         

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9.8 (494 Reviews)
Bed & Breakfast
  • Parking
  • Balcony/Terrace
  • Security/Safety
"Circa 1900 Home in Downtown Winona " From US $117
         

9.0 (7 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
The Exchange 13 | Historic Bldg, Studio, Dwntwn From US $170
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
The Exchange 25 | Historic Bldg, Studio, Dwntwn From US $159
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
The Exchange 15 | Historic Bldg, Studio, Dwntwn From US $170
         

9.6 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Historic Downtown Winona

Over 4+ Instantly Bookable Vacation Homes in or Near Historic Downtown Winona
Entire house rental From US $404
         

9.6 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Exchange 26 | Historic Bldg, 2 Bed, Dwntwn From US $242
         

9.6 (12 Reviews)
Apartment
  • TV
  • Security/Safety
  • Child Friendly
The Exchange 22 | Historic Bldg, 1 BR ADA, Dwntwn From US $260
         

9.6 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety

About Historic Downtown Winona Vacation Rentals

With more than 49 Historic Downtown Winona vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Yntravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Historic Downtown Winona.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Yntravel Historic Downtown Winona, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Historic Downtown Winona. Places to stay near Historic Downtown Winona are 400.66 ft² on average, with prices averaging $191 a night.

Yntravel makes it easy and safe to find and compare vacation rentals in Historic Downtown Winona with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Historic Downtown Winona

Type Count
Holiday Apartments 16
Hotels with Suites 12
Vacation Homes 12
B&B 4
Cottages 2
Cabin Rentals 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Historic Downtown Winona

Pro Tip: Yntravel makes it easy to compare the best listings on Yntravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Yntravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Historic Downtown Winona.

Weather in Historic Downtown Winona

View the weather forecast for Historic Downtown Winona before booking your Historic Downtown Winona Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Historic Downtown Winona Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Historic Downtown Winona?
Which vacation homes in Historic Downtown Winona are best for families?

If you are looking for a family-friendly vacation home in Historic Downtown Winona, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Historic Downtown Winona:

How many vacation rentals are available in Historic Downtown Winona?

Currently, the total number of properties listed in 2026 is over 49 in the Historic Downtown Winona area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Historic Downtown Winona.