Winona Holiday Rentals
House
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
Parking
Kitchen
Air Conditioner
Internet
US $98/Night
7 Nights - US $683
Apartment
9.0Exceptional
(39 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- Parking
- Air Conditioner
- Internet
Child Friendly
US $108/Night
7 Nights - US $758
Hotel
8.4Excellent
(1007 Reviews)
1 Bath
Breakfast- Parking
Pool- Kitchen
US $99/Night
7 Nights - US $690
Cabin
9.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
Hot Tub- Parking
Balcony/Terrace- Kitchen
US $212/Night
7 Nights - US $1,484
Apartment
- Hamilton
- ·
- Stoney Creek
- 0.91 mi to center
8.2Excellent
(61 Reviews)
3 Bedrooms
2 Baths
8 Guests
904.17 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $230/Night
7 Nights - US $1,612
Apartment
2 Bedrooms
2 Baths
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $109/Night
7 Nights - US $766
Villa
- Hamilton
- ·
- Stoney Creek
- 1.21 mi to center
10.0Exceptional
(4 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,716/Night
7 Nights - US $12,010
House
9.0Exceptional
(12 Reviews)
5 Bedrooms
6 Baths
16 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $957/Night
7 Nights - US $6,701
House
- Hamilton
- ·
- Stoney Creek
- 1.44 mi to center
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $549/Night
7 Nights - US $3,843
Luxury Holiday Rentals in Winona
Over 68+ Luxury Holiday Rentals in or Near Winona
House
- Hamilton
- ·
- Stoney Creek
- 1.26 mi to center
5.3Average
(3 Reviews)
6 Bedrooms
4 Baths
12 Guests
5995.5 ft²
- Hot Tub
- Air Conditioner
- Internet
- Child Friendly
US $1,205/Night
7 Nights - US $8,433
Villa
- Hamilton
- ·
- Stoney Creek
- 1.40 mi to center
3 Bedrooms
3 Baths
8 Guests
2368.06 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
US $567/Night
7 Nights - US $3,968
House
- Hamilton
- ·
- Stoney Creek
- 2.95 mi to center
5 Bedrooms
3 Baths
10 Guests
4500 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $379/Night
7 Nights - US $2,655
Apartment
- Hamilton
- ·
- Stoney Creek
- 1.07 mi to center
3 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $273/Night
7 Nights - US $1,912
House
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Air Conditioner
- Internet
- Child Friendly
US $239/Night
7 Nights - US $1,674
House
- Hamilton
- ·
- Stoney Creek
- 1.94 mi to center
4 Bedrooms
2 Baths
8 Guests
2340 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $227/Night
7 Nights - US $1,590
House
- Hamilton
- ·
- Stoney Creek
- 2.72 mi to center
3 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $208/Night
7 Nights - US $1,454
House
- Hamilton
- ·
- Stoney Creek
- 1.02 mi to center
3 Bedrooms
1 Bath
5 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $165/Night
7 Nights - US $1,154
Hotel
8.0Excellent
(330 Reviews)
1 Bath
269.1 ft²
Private Pool
Oceanfront- Parking
- Pool
US $104/Night
7 Nights - US $728
Top-Rated Holiday Rentals with a Pool in Winona
Over 5+ The Best Private Villas and Holiday Rentals in Winona with a Pool
Hotel
7.6Very Good
(1008 Reviews)
1 Bath
- Parking
- Pool
Spa- Kitchen
US $101/Night
7 Nights - US $709
Hotel
6.2Good
(340 Reviews)
4 Baths
325.61 ft²
- Private Pool
EV Charge Station- Parking
- Pool
US $95/Night
7 Nights - US $662
Villa
- Hamilton
- ·
- Stoney Creek
- 1.65 mi to center
4.6Average
(13 Reviews)
3 Bedrooms
3 Baths
8 Guests
3000 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $631/Night
7 Nights - US $4,416
Villa
- Hamilton
- ·
- Stoney Creek
- 1.67 mi to center
4.0Average
(6 Reviews)
5 Bedrooms
3 Baths
16 Guests
3300 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $624/Night
7 Nights - US $4,365
Cottage
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $287/Night
7 Nights - US $2,010
Pet-Friendly Holiday Rentals in Winona
Over 21+ Pet-Friendly Holiday Rentals in or Near Winona
House
- Hamilton
- ·
- Stoney Creek
- 0.87 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $175/Night
7 Nights - US $1,223
House
- Hamilton
- ·
- Stoney Creek
- 0.95 mi to center
5.2Average
(7 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $220/Night
7 Nights - US $1,540
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1634 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $137/Night
7 Nights - US $959
House
4 Bedrooms
2 Baths
10 Guests
- Air Conditioner
- Internet
Pet Friendly- Laundry
US $317/Night
7 Nights - US $2,220
Villa
- Hamilton
- ·
- Stoney Creek
- 0.95 mi to center
3 Bedrooms
3 Baths
10 Guests
1722 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $89/Night
7 Nights - US $621
House
5.0Average
(1 Review)
3 Bedrooms
3 Baths
5 Guests
1700 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $191/Night
7 Nights - US $1,337
House
- Hamilton
- ·
- Stoney Creek
- 0.95 mi to center
2.5Average
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
2153 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $254/Night
7 Nights - US $1,779
Cottage
6 Bedrooms
4 Baths
16 Guests
Ocean View- Balcony/Terrace
- View
- Kitchen
US $593/Night
7 Nights - US $4,149
House
- Hamilton
- ·
- Stoney Creek
- 1.38 mi to center
3 Bedrooms
3 Baths
8 Guests
900 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $348/Night
7 Nights - US $2,437
Large Holiday Rentals and Private Villas in Winona
Over 11+ Large Holiday Rentals and Private Villas in or Near Winona
House
- Hamilton
- ·
- Stoney Creek
- 2.09 mi to center
3 Bedrooms
2 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $198/Night
7 Nights - US $1,388
Villa
- Hamilton
- ·
- Stoney Creek
- 0.95 mi to center
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $118/Night
7 Nights - US $826
Villa
- Hamilton
- ·
- Stoney Creek
- 1.26 mi to center
4.4Average
(7 Reviews)
4 Bedrooms
3 Baths
8 Guests
5500 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $675/Night
7 Nights - US $4,725
Villa
3 Bedrooms
3 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $731/Night
7 Nights - US $5,116
Villa
4 Bedrooms
3 Baths
8 Guests
3600 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $569/Night
7 Nights - US $3,985
Villa
1 Bedroom
1 Bath
8 Guests
- Pet Friendly
- Child Friendly
US $323/Night
7 Nights - US $2,262
Villa
- Hamilton
- ·
- Stoney Creek
- 0.95 mi to center
3 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $320/Night
7 Nights - US $2,242
Villa
- Hamilton
- ·
- Stoney Creek
- 1.43 mi to center
1 Bedroom
1 Bath
8 Guests
- Pet Friendly
- Child Friendly
US $301/Night
7 Nights - US $2,108
House
- Hamilton
- ·
- Stoney Creek
- 0.92 mi to center
3 Bedrooms
3 Baths
10 Guests
2153 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $281/Night
7 Nights - US $1,969
Winona Private Villas and Holiday Homes Under $200
Over 20+ Winona Private Villas and Holiday Homes Under $200
Condo
- Hamilton
- ·
- Stoney Creek
- 1.02 mi to center
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $144/Night
7 Nights - US $1,008
Apartment
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $143/Night
7 Nights - US $1,001
Condo
- Hamilton
- ·
- Stoney Creek
- 1.02 mi to center
2 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $136/Night
7 Nights - US $954
House
1 Bedroom
1 Bath
4 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $105/Night
7 Nights - US $734
Apartment
1 Bedroom
2 Baths
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $88/Night
7 Nights - US $613
Hotel
1 Bath
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
US $144/Night
7 Nights - US $1,011
House
4 Bedrooms
4 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $193/Night
7 Nights - US $1,353
House
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $122/Night
7 Nights - US $852
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $128/Night
7 Nights - US $898
Instantly Bookable Holiday Homes in Winona
Over 12+ Instantly Bookable Holiday Homes in or Near Winona
House
- Hamilton
- ·
- Stoney Creek
- 2.76 mi to center
4 Bedrooms
2 Baths
9 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $222/Night
7 Nights - US $1,556
Cottage
- Hamilton
- ·
- Stoney Creek
- 1.12 mi to center
4.2Average
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Child Friendly
- Laundry
US $316/Night
7 Nights - US $2,211
Condo
4.0Average
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $264/Night
7 Nights - US $1,849
House
4.0Average
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $132/Night
7 Nights - US $925
Cottage
- Hamilton
- ·
- Stoney Creek
- 1.26 mi to center
3 Bedrooms
1 Bath
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $436/Night
7 Nights - US $3,053
House
- Hamilton
- ·
- Stoney Creek
- 1.02 mi to center
4 Bedrooms
4 Baths
6 Guests
3200 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $318/Night
7 Nights - US $2,228
House
- Hamilton
- ·
- Stoney Creek
- 0.95 mi to center
3 Bedrooms
3 Baths
7 Guests
1615 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $288/Night
7 Nights - US $2,015
Bed & Breakfast
2 Bedrooms
1 Bath
4 Guests
- Internet
- Laundry
Wellness Facilities
Security/Safety
US $257/Night
7 Nights - US $1,798
House
3 Bedrooms
3 Baths
10 Guests
2153 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $253/Night
7 Nights - US $1,774
Book a Last Minute Place to Stay in Winona
About Casai's Private Villas and Holiday Rentals in Winona
Discover more than 77 vacation rentals available in Winona. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winona.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winona, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winona. On average, places to stay near Winona offer 807.68 ft², with nightly prices averaging US $294.
With Casai, finding and comparing holiday rentals in Winona is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Winona
| Type | Count |
|---|---|
| Vacation Homes | 41 |
| Villas | 12 |
| Holiday Apartments | 8 |
| Cottages | 4 |
Use these Quick Filters to Find a Holiday Rental in Winona
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winona.
Weather in Winona, ON
View the weather forecast for Winona before booking your Winona Vacation Rentals to confirm your best time to go.
December - February
High 23°F Low 2°F
March - May
High 65°F Low 12°F
June - August
High 76°F Low 49°F
September - November
High 65°F Low 8°F
Frequently Asked Questions About Winona?
What are the top holiday rentals in Winona?
With numerous options available in Winona, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winona:
- Lakeside – Luxury Waterfront Retreat with Skyline Views
- Modern Bedroom with Private Bathroom in Niagara Region
- Spacious Guest Suite
- Million Dollar Private Lakefront House - Lake Patio - B&B - 250/248
- Luxury Tiny Home at the Farm - Botanical Oasis
- Quality Inn & Suites
- Lake-Walk House
- Quality Inn & Suites
- The Casablanca Hotel
- The Casablanca Hotel
Which holiday homes in Winona are best for families?
If you're searching for a family-friendly holiday home in Winona, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winona:
- Grimsby Luxe ~Spotless and Cozy ~Fresh Linens
- Luxury & Spacious 4BR ~ Stoney Creek ~ Hamilton
- Staycation StoneyCreek- 3Bdrm-Hotub-BBQ-Lakeside-
How many Casai.com holiday rentals are available in Winona?
As of 2026, Casai boasts over 77 properties listed in the Winona area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winona.
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