Vacation Rentals in Winona, ON: Compare 10+ Sites & Save

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50 Best Vacation Rentals in Winona (Starting from $64)

Spacious Guest Suite
Spacious Guest Suite
Apartment
Hamilton, Canada
1.7k from Winona center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
9.3

Superb

18 reviews

$64
Average price / night
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Modern and Luxurious - 28 Minutes from Niagara Falls!
Modern and Luxurious - 28 Minutes from Niagara Falls!
House
Hamilton, L8E 0G4, Canada
0.9k from Winona center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
New to Booking
$182
Average price / night
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Lakeside Villa
Lakeside Villa
Villa
Hamilton, Canada
2.9k from Winona center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

6 Bedrooms12 Guests
5.5

Review score

2 reviews

$1204
Average price / night
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Modern 3BR/2.5 Bath House Minutes to Niagara Falls
Modern 3BR/2.5 Bath House Minutes to Niagara Falls
House
Hamilton, L8E 0L1, Canada
1.0k from Winona center

AC, Dryer, Heater, Laundry, No Smoking, Washer

3 Bedrooms8 Guests
New to Booking
$465
Average price / night
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Lakeview Villa - Enjoy luxury Vacation at its Best!
Lakeview Villa - Enjoy luxury Vacation at its Best!
Villa
Hamilton, Canada
2.9k from Winona center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$258
Average price / night
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Private Waterfront Paradise Home on Lake Ontario!
Private Waterfront Paradise Home on Lake Ontario!
House
Hamilton, L8E 5T3, Canada
1.8k from Winona center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$191
Average price / night
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Executive 3 Bedroom townhouse close to the Lake
Executive 3 Bedroom townhouse close to the Lake
Villa
Hamilton, Canada
3.3k from Winona center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
5.5

Review score

2 reviews

$321
Average price / night
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Lake Vista Family Retreat
Lake Vista Family Retreat
House
Hamilton, L8E 0C7, Canada
2.2k from Winona center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
New to Booking
$314
Average price / night
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Luxury 3BR 2BA Townhome with Private HOT TUB, Gym, BBQ by GLOBALSTAY
Luxury 3BR 2BA Townhome with Private HOT TUB, Gym, BBQ by GLOBALSTAY
Apartment
Hamilton, Canada
3.3k from Winona center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

3 Bedrooms10 Guests
7.0

Good

51 reviews

$240
Average price / night
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Grimsby Luxe ~Spotless and Cozy ~Fresh Linens
Grimsby Luxe ~Spotless and Cozy ~Fresh Linens
House
Grimsby, L3M 0H4, Canada
2.9k from Winona center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$228
Average price / night
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lake house
lake house
Apartment
Winona, Ontario, Canada
3.4k from Winona center

Air Conditioner, Internet, Parking

1 Bedroom2 Guests
New to Booking
$135
Average price / night
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Luxury Curated Stay – Steps from Lake Ontario
Luxury Curated Stay – Steps from Lake Ontario
House
Hamilton, L8E 5C3, Canada
2.9k from Winona center

AC, Free Parking, Internet, No Smoking, Patio, TV

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$214
Average price / night
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Lake-Walk House 3 Bed 2 Bath Apt
Lake-Walk House 3 Bed 2 Bath Apt
Apartment
Hamilton, Canada
3.9k from Winona center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms8 Guests
8.4

Very Good

46 reviews

$334
Average price / night
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Lake Walk House a 3 Bed 2 Bath Basement Apartment in the Golden Horseshoe
Lake Walk House a 3 Bed 2 Bath Basement Apartment in the Golden Horseshoe
Apartment
Hamilton, L8E 5A3, Canada
4.3k from Winona center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms8 Guests
New to Booking
$244
Average price / night
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Lovely apartment house
Lovely apartment house
Apartment
Grimsby, Canada
6.4k from Winona center

Apartments, Cheap, Accommodations, Parking, 3-star, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms5 Guests
9.0

Fabulous

31 reviews

$178
Average price / night
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Cozy 1 Bedroom 1 Bath in Niagara Region
Cozy 1 Bedroom 1 Bath in Niagara Region
House
Grimsby, L3M 0H2, Canada
4.3k from Winona center

AC, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$87
Average price / night
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GLOBALSTAY Waterfront 20Ppl 5 Bedroom Townhouse Hot tub Sauna
GLOBALSTAY Waterfront 20Ppl 5 Bedroom Townhouse Hot tub Sauna
House
Hamilton, Canada
6.4k from Winona center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

5 Bedrooms20 Guests
7.7

Good

36 reviews

$487
Average price / night
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Million Dollar Private Lakefront House - Lake Patio - B&B - 250/248
Million Dollar Private Lakefront House - Lake Patio - B&B - 250/248
House
GRIMSBY, L3M4E8, Canada
4.8k from Winona center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Laundry

5 Bedrooms16 Guests
9.0

Fabulous

12 reviews

$858
Average price / night
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SAI GON Suit
SAI GON Suit
Apartment
Grimsby, Canada
7.6k from Winona center

Fireplace/Heating, Security/Safety, Internet, Parking, Air Conditioner, Child Friendly

2 Bedrooms4 Guests
8.8

Fabulous

12 reviews

$97
Average price / night
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The space, privacy, and comfort of a true home away from home in Niagara area.
The space, privacy, and comfort of a true home away from home in Niagara area.
House
Grimsby, L3M 5L9, Canada
5.1k from Winona center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

5 Bedrooms6 Guests
New to Booking
$208
Average price / night
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Lovely 1- bedroom Unit in Grimsby
Lovely 1- bedroom Unit in Grimsby
Apartment
Grimsby, Canada
7.6k from Winona center

Security/Safety, Internet, Parking, Air Conditioner, Child Friendly

1 Bedroom2 Guests
9.5

Superb

2 reviews

$74
Average price / night
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Luxury Million $$$ Lakefront Estate House - Swimming Pool - Bed and Breakfast
Luxury Million $$$ Lakefront Estate House - Swimming Pool - Bed and Breakfast
House
Grimsby, L3M 4E8, Canada
5.3k from Winona center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms16 Guests
9.8

Exceptional

8 reviews

$972
Average price / night
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Lakehouse with Spectacular View + Pool and 5 Bedrooms close to Niagara Falls
Lakehouse with Spectacular View + Pool and 5 Bedrooms close to Niagara Falls
House
Grimsby, L3M 4E8, Canada
5.5k from Winona center

AC, Fireplace, Heater, Internet, Laundry, No Smoking, Patio, Washer

5 Bedrooms12 Guests
9.8

Exceptional

8 reviews

$525
Average price / night
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Lakefront Lower Level Walkout- 35 min to Niagara
Lakefront Lower Level Walkout- 35 min to Niagara
House
Grimsby, L3M 5C8, Canada
5.9k from Winona center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
New to Booking
$254
Average price / night
Check Availability
Stoney Creek 4BR|3BA Nature Oasis | Sauna, Games & Luxe Comfort | Smart TV
Stoney Creek 4BR|3BA Nature Oasis | Sauna, Games & Luxe Comfort | Smart TV
House
Hamilton, L8G 3E1, Canada
6.3k from Winona center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$415
Average price / night
Check Availability
GLOBALSTAY. 20 Ppl 5BR Townhome on the Lake. HotTub, Gym, BBQ
GLOBALSTAY. 20 Ppl 5BR Townhome on the Lake. HotTub, Gym, BBQ
Villa
Hamilton/Canada, L8E0J4, Canada
6.5k from Winona center

AC, Barbecue, Crib, Dryer, Elevator, Extra Bed, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms20 Guests
New to Booking
$300
Average price / night
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GLOBALSTAY. Waterfront 5BR Townhouse. Private HOT TUB, Gym, Sauna
GLOBALSTAY. Waterfront 5BR Townhouse. Private HOT TUB, Gym, Sauna
Apartment
114 Shoreview Pl, Hamilton, L8E 0J4, Canada
6.5k from Winona center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

9.0

Fabulous

14 reviews

$490
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Winona.

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Frequently Asked Questions

You can explore 50 verified vacation rentals in Winona. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Winona vary depending on the season, property size, and location. Rates typically start from around $64 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Winona include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Winona welcome pets. Currently, 16 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Winona often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.