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

Canad Inns Destination Centre Transcona

3 out of 5
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

Canad Inns Destination Centre Fort Garry

3 out of 5
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

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
Price was $1,325, price is now $1,156 per person
$1,156
per person
Jul 29 - Aug 3
found 7 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

Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was $1,158, price is now $1,013 per person
$1,013
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
8.4/10 Very Good! (3,021 reviews)
Room was clean and awesome staff

Reviewed on May 13, 2026

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $1,201, price is now $1,061 per person
$1,061
per person
Jul 29 - Aug 3
found 7 hours ago
Roundtrip flight included
Chicago (ORD) to Winnipeg (YWG)
8.4/10 Very Good! (1,593 reviews)
Clean room and staff are very nice

Reviewed on May 8, 2026

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Oak Point Hotel Deals

Lakefront Cabin

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

Lakefront Cabin
Charming Lakeview cabin in a peaceful bay

Charming Lakeview cabin in a peaceful bay

Saint Laurent MB
$255 nightly
The price is $285 total per night from May 26 to May 27
$285 total
May 26 - May 27
Total with taxes and fees
10/10 Exceptional! (3 reviews)
Awesome perfect place to relax

Reviewed on Aug 31, 2025

Charming Lakeview cabin in a peaceful bay
Hidden paradise! Amazing Sunsets and spa! $200 and up.

Hidden paradise! Amazing Sunsets and spa! $200 and up.

Twin Lake Beach MB
Get rates
Hidden paradise! Amazing Sunsets and spa! $200 and up.
See all 18 properties in Oak Point
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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Frequently asked questions

How much does an Oak Point vacation package cost?
You'll find cheap prices from $881 on Expedia for your Oak Point getaway. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Oak Point costs.
What are the cheapest months to go to Oak Point?
You can generally find lower rates and better availability in December, January and February. Check out our cheap Oak Point vacation packages and you could get some great off-season discounts.
How many days is enough for Oak Point?
Usually, a handful of days is enough to check out the top sights during your Oak Point vacation. However, if you want to have time to chill out or go on day tours, think about extending your trip.
How to find the best Oak Point package deals?
Begin your search for an Oak Point package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Oak Point package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oak Point adventure underway.
Is it cheaper to book an Oak Point vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights individually. Better still, you can tailor your Oak Point trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Oak Point?
Secure fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Oak Point getaway.
Does Expedia offer Book Now, Pay Later Oak Point vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Oak Point break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.