Oak Point Vacations from $481

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The Latest Oak Point vacation packages

Price found within the past 48 hours. Click for updated prices.
Sandman Hotel & Suites Winnipeg Airport

Sandman Hotel & Suites Winnipeg Airport

3 out of 5
St. James
Price was $564, price is now $481 per person
$481
per person
Feb 14 - Feb 16
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Winnipeg (YWG)
8.2/10 Very Good! (1,408 reviews)
Everything was great

Reviewed on Jan 13, 2026

Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was $695, price is now $542 per person
$542
per person
Feb 14 - Feb 16
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Winnipeg (YWG)
8.4/10 Very Good! (2,464 reviews)
The room was very clean. The staff was helpful. But be warned; on the 3rd floor we were given a room and right outside was a big loud, maybe an air conditioner or some large loud unit. So even though the bed was comfortable we did not sleep much or well. I will be on guard for that in our next stay. We enjoyed everything else about the hotel so I will be staying again.

Reviewed on Jan 12, 2026

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $574, price is now $489 per person
$489
per person
Feb 14 - Feb 16
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Winnipeg (YWG)
8.2/10 Very Good! (1,479 reviews)
I stayed four nights consecutively. I would have liked a variety of fruit... only apples provided and the same yogurt fruit cocktail... boring

Reviewed on Jan 13, 2026

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $567, price is now $493 per person
$493
per person
Feb 14 - Feb 16
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Winnipeg (YWG)
8/10 Very Good! (1,105 reviews)
The rooms are always clean and the staff are very friendly and helpful. I love staying here. There are a lot of stores close by if you need anything in your room. They have altos or The Tavern united for after hours hunger.

Reviewed on Jan 9, 2026

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
Price was $564, price is now $491 per person
$491
per person
Feb 14 - Feb 16
found 21 hours ago
Roundtrip non-stop flight included
New York (NYC) to Winnipeg (YWG)
9/10 Wonderful! (1,380 reviews)
Staff was very accommodating

Reviewed on Jan 13, 2026

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Oak Point Hotel Deals

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

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

Saint Laurent MB
9.4/10 Exceptional! (49 reviews)
Started off with a bit of a hiccup but the host did her best to rectify the situation and made it up to us. Overall the stay was awesome. They have a beautiful place that relax. The sauna was amazing and so nice to use in the winter.

Reviewed on Dec 31, 2025

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

Charming Lakeview cabin in a peaceful bay

Saint Laurent MB
10/10 Exceptional! (3 reviews)
Awesome perfect place to relax

Reviewed on Aug 31, 2025

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Charming Lakeview cabin in a peaceful bay
Come enjoy peace and tranquillity at Pirate Bay

Come enjoy peace and tranquillity at Pirate Bay

St.Laurent MB
10/10 Exceptional! (13 reviews)
The cabin was as presented in the photos and all beds are comfortable. The kitchen\living room layout is just right; the barbecue is just off the deck in the big, beautiful backyard. The cabin is well looked after clean. Just a short drive or 20 minute walk to the lovely beach. If we needed anything, ...

Reviewed on Aug 15, 2025

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Come enjoy peace and tranquillity at Pirate Bay
See all 14 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 $481 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.