
Oak Point Vacations from $881
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The Latest Oak Point vacation packages
Price found within the past 48 hours. Click for updated prices.

Canad Inns Destination Centre Transcona
Transcona
Price was $1,005, price is now $881 per person
$881
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
8.4/10 Very Good! (1,005 reviews)
The room was spacious. There was a mini fridge, no freezer. There were receptacles for charging your cell phone. They had shampoo, conditioner and body wash in the tub area. No makeup remover or shower cap, but I didn't ask for them. May have an iron at the front but not sure. Staff was friendly. No break
Reviewed on May 12, 2026

Canad Inns Destination Centre Fort Garry
Fort Garry
Price was $1,039, price is now $903 per person
$903
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
8/10 Very Good! (1,292 reviews)
The suite was nice for the price we got. The bed was comfortable and the staff were good. The only complaint was the pool had such a strong smell of chlorine, that my husband and I didn't want to use the pool or hot tub.
Reviewed on May 12, 2026

Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was $1,325, price is now $1,156 per person
$1,156
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
9/10 Wonderful! (1,636 reviews)
Breakfast was good and quite reasonably priced
Reviewed on May 13, 2026


Humphry Inn & Suites
Downtown Winnipeg
Price was $1,201, price is now $1,061 per person
$1,061
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
8.4/10 Very Good! (1,593 reviews)
Rooms were fine and location was okay. It's quite convenient if you're arriving or departing by VIA Rail, as Union Station is just a block or two away.
The breakfast is a bit hit and miss but overall pretty good. Cereals, yogurt, canned fruit cocktail and plenty of bread options including English muffins.
There are hot choices each morning but only two, which leads to some odd combinations. One morning the hot breakfast options consisted of just hashbrowns and bacon -- no eggs. The next day it was tiny pancakes with sausages. The eggs made an appearance the third day in the form of a nice little omelette with ham slices as the second hot option. On the fourth day there were egg patties and sausage patties but the cold cereals had disappeared from the buffet. So it can be slightly erratic.
Reviewed on May 13, 2026
Oak Point Hotel Deals

Lakefront Cabin
St. Laurent MB
$180 nightly
The price is $201 total per night from May 18 to May 19
$201 total
May 18 - May 19
Total with taxes and fees
8.8/10 Excellent! (15 reviews)
We had a great time!
Reviewed on Sep 1, 2025

Charming Lakeview cabin in a peaceful bay
Saint Laurent MB
$237 nightly
The price is $265 total per night from May 14 to May 15
$265 total
May 14 - May 15
Total with taxes and fees
10/10 Exceptional! (3 reviews)
Awesome perfect place to relax
Reviewed on Aug 31, 2025

Hidden paradise! Amazing Sunsets and spa! $200 and up.
Twin Lake Beach MB
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Oak Point Vacation Packages
Oak Point Essential Information
Language | English |
|---|---|
Currency | Canadian dollars |
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