Search Deals onHillside Beach Vacation Packages
Hillside Beach Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Canad Inns Destination Centre Windsor Park
Price was $791, price is now $721 per person
$721
per person
Dec 1 - Dec 4
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this family-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.
Humphry Inn & Suites
Price was $883, price is now $776 per person
$776
per person
Dec 1 - Dec 4
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.
Nice hotel. Clean. Large room with a king bed. The area is safe during the day but I would not go walking at night. As others have noted, the gym has no weights at all. Breakfast are OK but could use some improvement. Like low-fat milk, fresh fruit. The fruit consisted of apples and canned fruit cocktail. Most hotels would serve fresh fruit. It was nice to finally have cooked eggs on the last day of my stay. All other days there was bacon or sausages. As I said, a better quality breakfast would be an asset.
Reviewed on Oct 13, 2026
Inn At The Forks
Price was $1,086, price is now $961 per person
$961
per person
Dec 1 - Dec 4
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this spa hotel in Winnipeg. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.
Staff were welcoming and helpful. Room was clean. Nice veiw. Convenient location
Reviewed on Oct 13, 2026
Hyatt House Winnipeg-South/Outlet Collection
Price was $1,081, price is now $982 per person
$982
per person
Dec 1 - Dec 4
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Outlet Collection Winnipeg and Polo Park are located nearby.
I will stay here again.
Reviewed on Oct 13, 2026
Canad Inns Destination Centre Transcona
Price was $805, price is now $738 per person
$738
per person
Dec 1 - Dec 4
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this family-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Canada Life Centre and Transcona Golf Club are located nearby.
Norwood Hotel
Price was $891, price is now $819 per person
$819
per person
Dec 1 - Dec 4
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.
Canad Inns Destination Centre Club Regent Casino Hotel
Price was $833, price is now $773 per person
$773
per person
Dec 1 - Dec 4
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Canada Life Centre and Club Regent Casino are located nearby.
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
Price was $886, price is now $826 per person
$826
per person
Dec 1 - Dec 4
found 2 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this spa hotel in Winnipeg. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.
Hillside Beach Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Hillside Beach Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Nov 28 - Fri, Dec 11
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$219 Roundtrip, found 4 hours ago
$219
Roundtrip
found 4 hours ago
Wed, Oct 28 - Fri, Oct 30
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$241 Roundtrip, found 3 hours ago
$241
Roundtrip
found 3 hours ago
Mon, Nov 2 - Wed, Nov 4
YEG
Edmonton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$315 Roundtrip, found 4 days ago
$315
Roundtrip
found 4 days ago
Tue, Dec 15 - Thu, Dec 24
YOW
Macdonald-Cartier Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$383 Roundtrip, found 7 hours ago
$383
Roundtrip
found 7 hours ago
Discover Other Travel Deals
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
