Hillside Beach Vacations from $672

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Your Hillside Beach Vacation

The hassle-free way to experience this city is with a customized Hillside Beach vacation package. Stay in the neighborhood of Grand Beach, which is great for families, nature and watersports or go someplace else — our packages are all about you. Eager to do some sightseeing but don't know where to start? Every trip to Hillside Beach should include Elk Island Provincial Park. That dream Hillside Beach vacation is a few clicks away. Explore accommodations, flights and more on Expedia for a trip that's tailored just for you.

The Latest Hillside Beach vacation packages

Price found within the past 48 hours. Click for updated prices.
Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $721, price is now $672 per person
$672
per person
Mar 12 - Mar 14
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
8/10 Very Good! (1,105 reviews)
Hot tub wasn't working and closed the pool early just to test the clorine

Reviewed on Jan 5, 2026

Sandman Signature Winnipeg Airport Hotel & Suites

Sandman Signature Winnipeg Airport Hotel & Suites

4 out of 5
St. James
Price was $823, price is now $743 per person
$743
per person
Mar 12 - Mar 14
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
9/10 Wonderful! (195 reviews)
Nice and clean rite by the airport!

Reviewed on Jan 7, 2026

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $752, price is now $689 per person
$689
per person
Mar 12 - Mar 14
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
8.2/10 Very Good! (1,479 reviews)
Room was spacious and clean. Room was Facing the street. Heard a humming noise all night. Didn’t sleep well. There was a continental breakfast with two hot item. They were not good at all. Available paid parking on site. I’m 50/50 on if I would stay there again.

Reviewed on Jan 5, 2026

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
Price was $733, price is now $680 per person
$680
per person
Mar 12 - Mar 14
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
7.8/10 Good! (1,002 reviews)
The room was good condition but did not have a soap dispenser rather a bar of soap but no soap dish the bar of soap got stuck to the counter then I had no soap to use that was dissapointing. The hot tub was not good at all very low water and the pressure and heat was not great. Other then that everything was okay.

Reviewed on Jan 5, 2026

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $729, price is now $678 per person
$678
per person
Mar 12 - Mar 14
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
8.4/10 Very Good! (1,001 reviews)
Nice room, quick service,

Reviewed on Jan 6, 2026

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Hillside Beach Hotel Deals

Cozy wooded cottage, with stunning tree-top views & 3 mins from the beach!

Cozy wooded cottage, with stunning tree-top views & 3 mins from the beach!

Victoria Beach MB
9.6/10 Exceptional! (19 reviews)
Amazing location and comfortable, cozy rooms. Enough space for the whole family without it feeling crowded - the dogs loved sitting out on the deck and great trails close by!

Reviewed on Oct 20, 2025

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Cozy wooded cottage, with stunning tree-top views & 3 mins from the beach!
Charming 3-bedroom cottage with WiFi and AC in fabulous Hillside/Victoria Beach

Charming 3-bedroom cottage with WiFi and AC in fabulous Hillside/Victoria Beach

Victoria Beach MB
9.6/10 Exceptional! (13 reviews)
Very nice place for vacation.

Reviewed on Sep 22, 2025

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Charming 3-bedroom cottage with WiFi and AC in fabulous Hillside/Victoria Beach
Lakefront cottage - two decks overlooking Lake Winnipeg

Lakefront cottage - two decks overlooking Lake Winnipeg

Hillside Beach MB
7.6/10 Good! (16 reviews)
Cottage could probably use some maintenance, but overall it was clean and well equipped. I was happy that the rotten floor of the outdoor shower had been removed. I really enjoy that shower. As ever, we loved the deck that overlooks the lake. I will be renting again next year.

Reviewed on Sep 26, 2025

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Lakefront cottage - two decks overlooking Lake Winnipeg
See all 118 properties in Hillside Beach
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 Hillside Beach Vacation Packages

Hillside Beach Essential Information

Language
English
Currency
Canadian dollars
Top Sights
Grand Beach Provincial Park and Elk Island Provincial Park

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Frequently asked questions

How much does a Hillside Beach vacation package cost?
You can snap up a vacation package to this popular destination from $672 on Expedia. But how much your vacation to Hillside Beach costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Hillside Beach?
December, January and February are the best times to look for cheap Hillside Beach vacation packages. Traveling in less busy months means you can typically find reduced prices on accommodations and flights.
How many days is enough for Hillside Beach?
The ideal duration of your Hillside Beach vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you time to check out all the major sights and discover some hidden treasures along the way.
How to find the best Hillside Beach package deals?
Begin your search for a Hillside Beach package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Hillside Beach package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Hillside Beach adventure underway.
Is it cheaper to book a Hillside Beach vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and stays individually. Better still, you can tailor your Hillside Beach trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Hillside Beach?
If you're considering a spontaneous Hillside Beach adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Hillside Beach vacation packages?
Your Hillside Beach getaway should be an escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.