Winona Holiday Rentals
10.0
Exceptional
(1 Review)
- Hamilton
- Stoney Creek
- 0.87 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Pet Friendly
House
- Balcony/Terrace
- Pet Friendly
- Parking
د.إ.822/Night
For 7 Nights د.إ.5,758
9.3
Exceptional
(18 Reviews)
699.65 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Parking
- Air Conditioner
- Internet
د.إ.398/Night
For 7 Nights د.إ.2,784
8.4
Excellent
(1003 Reviews)
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
د.إ.339/Night
For 7 Nights د.إ.2,369
9.6
Exceptional
(8 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
د.إ.704/Night
For 7 Nights د.إ.4,925
9.0
Exceptional
(95 Reviews)
301.39 ft²
4 Guests
2 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
د.إ.294/Night
For 7 Nights د.إ.2,057
New
- Hamilton
- Stoney Creek
- 2.72 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
د.إ.1,303/Night
For 7 Nights د.إ.9,119
New
- Hamilton
- Stoney Creek
- 1.07 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
د.إ.916/Night
For 7 Nights د.إ.6,412
New
- Hamilton
- Stoney Creek
- 1.94 mi to center
2340 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Air Conditioner
د.إ.768/Night
For 7 Nights د.إ.5,377
New
1500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.708/Night
For 7 Nights د.إ.4,954
Luxury Holiday Rentals in Winona
Over 73+ Luxury Holiday Rentals in or Near Winona
7.3
Very Good
(333 Reviews)
325.61 ft²
4 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
د.إ.4,484/Night
For 7 Nights د.إ.31,389
5.5
Average
(2 Reviews)
- Hamilton
- Stoney Creek
- 1.26 mi to center
5995.5 ft²
12 Guests
6 Bedrooms
3 Bathrooms
Free Cancellation
Villa
- Parking
- Air Conditioner
- Internet
د.إ.4,424/Night
For 7 Nights د.إ.30,970
10.0
Exceptional
(3 Reviews)
- Hamilton
- Stoney Creek
- 1.21 mi to center
12 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
د.إ.3,643/Night
For 7 Nights د.إ.25,502
9.0
Exceptional
(12 Reviews)
16 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Kitchen
د.إ.3,239/Night
For 7 Nights د.إ.22,674
New
- Hamilton
- Stoney Creek
- 2.66 mi to center
1205.56 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Parking
- Air Conditioner
د.إ.2,121/Night
For 7 Nights د.إ.14,848
New
- Hamilton
- Stoney Creek
- 1.40 mi to center
2368.06 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Balcony/Terrace
- View
- Pet Friendly
د.إ.2,082/Night
For 7 Nights د.إ.14,572
8.8
Fabulous
(4 Reviews)
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Villa
- Balcony/Terrace
- View
- Parking
د.إ.1,324/Night
For 7 Nights د.إ.9,269
8.1
Excellent
(53 Reviews)
- Hamilton
- Stoney Creek
- 0.91 mi to center
904.17 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Parking
- Air Conditioner
- Internet
د.إ.1,204/Night
For 7 Nights د.إ.8,425
New
- Hamilton
- Stoney Creek
- 2.95 mi to center
4500 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,186/Night
For 7 Nights د.إ.8,304
Top-Rated Holiday Rentals with a Pool in Winona
Over 5+ The Best Private Villas and Holiday Rentals in Winona with a Pool
7.8
Very Good
(1002 Reviews)
1 Bathroom
Family Friendly
Hotel
- Spa
- Pool
- Kitchen
د.إ.402/Night
For 7 Nights د.إ.2,813
7.6
Very Good
(302 Reviews)
269.1 ft²
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
د.إ.365/Night
For 7 Nights د.إ.2,556
4.6
Average
(13 Reviews)
- Hamilton
- Stoney Creek
- 1.65 mi to center
3000 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
د.إ.2,317/Night
For 7 Nights د.إ.16,218
4.0
Average
(6 Reviews)
- Hamilton
- Stoney Creek
- 1.67 mi to center
3300 ft²
16 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
د.إ.2,290/Night
For 7 Nights د.إ.16,030
New
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Cottage
- Private Pool
- Pool
- Balcony/Terrace
د.إ.1,055/Night
For 7 Nights د.إ.7,382
Pet-Friendly Holiday Rentals in Winona
Over 20+ Pet-Friendly Holiday Rentals in or Near Winona
10.0
Exceptional
(1 Review)
1634 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.503/Night
For 7 Nights د.إ.3,522
5.2
Average
(7 Reviews)
- Hamilton
- Stoney Creek
- 0.95 mi to center
7 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
د.إ.808/Night
For 7 Nights د.إ.5,656
5.0
Average
(1 Review)
1700 ft²
5 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.701/Night
For 7 Nights د.إ.4,910
2.5
Average
(2 Reviews)
- Hamilton
- Stoney Creek
- 0.95 mi to center
2153 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.933/Night
For 7 Nights د.إ.6,533
New
- Hamilton
- Stoney Creek
- 1.38 mi to center
900 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- Pet Friendly
د.إ.1,279/Night
For 7 Nights د.إ.8,950
New
8 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Pet Friendly
- Child Friendly
د.إ.1,187/Night
For 7 Nights د.إ.8,307
New
- Hamilton
- Stoney Creek
- 1.02 mi to center
3200 ft²
6 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
د.إ.1,169/Night
For 7 Nights د.إ.8,182
New
- Hamilton
- Stoney Creek
- 1.43 mi to center
8 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Pet Friendly
- Child Friendly
د.إ.1,106/Night
For 7 Nights د.إ.7,742
New
- Hamilton
- Stoney Creek
- 0.95 mi to center
1615 ft²
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,057/Night
For 7 Nights د.إ.7,400
Large Holiday Rentals and Private Villas in Winona
Over 13+ Large Holiday Rentals and Private Villas in or Near Winona
4.4
Average
(7 Reviews)
- Hamilton
- Stoney Creek
- 1.26 mi to center
5500 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Balcony/Terrace
- Kitchen
- Air Conditioner
د.إ.2,479/Night
For 7 Nights د.إ.17,353
New
- Hamilton
- Stoney Creek
- 1.26 mi to center
4004.17 ft²
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
Villa
- Parking
- Air Conditioner
- Internet
د.إ.948/Night
For 7 Nights د.إ.6,633
New
- Hamilton
- Stoney Creek
- 0.95 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.434/Night
For 7 Nights د.إ.3,033
New
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Balcony/Terrace
- Kitchen
- Air Conditioner
د.إ.2,684/Night
For 7 Nights د.إ.18,789
New
- Hamilton
- Stoney Creek
- 0.92 mi to center
2153 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,033/Night
For 7 Nights د.إ.7,231
New
2153 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.931/Night
For 7 Nights د.إ.6,515
New
- Hamilton
- Stoney Creek
- 2.09 mi to center
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
د.إ.728/Night
For 7 Nights د.إ.5,097
New
- Hamilton
- Stoney Creek
- 0.95 mi to center
1722 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Hot Tub
- Spa
- Fireplace/Heating
د.إ.326/Night
For 7 Nights د.إ.2,281
New
16 Guests
6 Bedrooms
4 Bathrooms
Ocean View
Cottage
- Ocean View
- Balcony/Terrace
- View
د.إ.2,177/Night
For 7 Nights د.إ.15,237
Winona Private Villas and Holiday Homes Under $200
Over 25+ Winona Private Villas and Holiday Homes Under $200
New
4 Guests
2 Bedrooms
2 Bathrooms
Couples Retreat
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
د.إ.322/Night
For 7 Nights د.إ.2,259
New
8 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- View
- Parking
- Air Conditioner
د.إ.549/Night
For 7 Nights د.إ.3,841
New
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
House
- Fireplace/Heating
- Parking
- Air Conditioner
د.إ.321/Night
For 7 Nights د.إ.2,251
New
6458.35 ft²
2 Guests
1 Bedroom
2 Bathrooms
Apartment
- Parking
- Air Conditioner
- Internet
د.إ.496/Night
For 7 Nights د.إ.3,471
New
6 Guests
3 Bedrooms
2 Bathrooms
House
- Hot Tub
- Fireplace/Heating
- Air Conditioner
د.إ.731/Night
For 7 Nights د.إ.5,116
4.0
Average
(1 Review)
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
د.إ.486/Night
For 7 Nights د.إ.3,397
New
- Hamilton
- Stoney Creek
- 1.06 mi to center
5 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Air Conditioner
- Internet
- Child Friendly
د.إ.674/Night
For 7 Nights د.إ.4,719
New
1500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
د.إ.537/Night
For 7 Nights د.إ.3,757
New
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.525/Night
For 7 Nights د.إ.3,676
Instantly Bookable Holiday Homes in Winona
Over 9+ Instantly Bookable Holiday Homes in or Near Winona
4.2
Average
(5 Reviews)
- Hamilton
- Stoney Creek
- 1.12 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Kitchen
- Air Conditioner
- Child Friendly
د.إ.1,160/Night
For 7 Nights د.إ.8,120
4.0
Average
(1 Review)
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
د.إ.970/Night
For 7 Nights د.إ.6,790
New
- Hamilton
- Stoney Creek
- 1.26 mi to center
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Lake View
- Balcony/Terrace
د.إ.1,602/Night
For 7 Nights د.إ.11,212
New
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Internet
- Child Friendly
د.إ.943/Night
For 7 Nights د.إ.6,603
New
- Hamilton
- Stoney Creek
- 2.76 mi to center
9 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
د.إ.816/Night
For 7 Nights د.إ.5,714
New
3767 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Child Friendly
د.إ.484/Night
For 7 Nights د.إ.3,386
New
800 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.385/Night
For 7 Nights د.إ.2,696
New
2 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Air Conditioner
- Internet
- Child Friendly
د.إ.322/Night
For 7 Nights د.إ.2,251
New
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Air Conditioner
- Internet
د.إ.530/Night
For 7 Nights د.إ.3,713
Book a Last Minute Place to Stay in Winona
About Casai's Private Villas and Holiday Rentals in Winona
Discover more than 82 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 924.09 ft², with nightly prices averaging د.إ.1,072.
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.
Show more
Show less
Top Accommodation Types in Winona
| Type | Count |
|---|---|
| Vacation Homes | 40 |
| Villas | 16 |
| Holiday Apartments | 10 |
| 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
- Luxury Curated Stay – Steps from Lake Ontario
- Luxury Tiny Home at the Farm - Botanical Oasis
- Spacious Guest Suite
- Jahsavvy's Nest
- Million Dollar Private Lakefront House - Lake Patio - B&B - 250/248
- Lakefront cheerful 2 bedroom cottage house
- Quality Inn & Suites
- Lake-Walk House 3 Bed 2 Bath Apt
- 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:
- Luxury & Spacious 4BR ~ Stoney Creek ~ Hamilton
- Grimsby on the Lake sweet, your perfect retreat
- Professional Three Bedroom Condo Suite
How many Casai.ae holiday rentals are available in Winona?
As of 2026, Casai boasts over 82 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.
People Also Ask
Finding the best prices in Winona
Map
