Milestone Vacations from $595

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The Latest Milestone vacation packages

Price found within the past 48 hours. Click for updated prices.
Wingate By Wyndham Regina

Wingate By Wyndham Regina

3 out of 5
Downtown Regina
Price was $636, price is now $595 per person
$595
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Regina (YQR)
8.6/10 Excellent! (1,156 reviews)
Breakfast was limited

Reviewed on Jun 19, 2026

Sandman Hotel & Suites Regina

Sandman Hotel & Suites Regina

3 out of 5
Price was $714, price is now $620 per person
$620
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Regina (YQR)
8.6/10 Excellent! (1,071 reviews)
What a beautiful, clean, outstanding hotel and the liveliest of staff I will stay here again absolutely in Regina beautiful beautiful

Reviewed on Jun 22, 2026

Home Inn and Suites Regina Airport

Home Inn and Suites Regina Airport

2.5 out of 5
Harbour Landing
Price was $671, price is now $619 per person
$619
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Regina (YQR)
9/10 Wonderful! (1,310 reviews)
Staff is always friendly and welcoming. Room was very clean.

Reviewed on Jun 21, 2026

Home Inn & Suites Regina East

Home Inn & Suites Regina East

2.5 out of 5
Price was $670, price is now $625 per person
$625
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Regina (YQR)
9/10 Wonderful! (1,070 reviews)
Staff were helpful and friendly. The room was clean.

Reviewed on Jun 21, 2026

Four Points By Sheraton Regina

Four Points By Sheraton Regina

3 out of 5
Price was $638, price is now $598 per person
$598
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Regina (YQR)
8/10 Very Good! (1,002 reviews)
The room was clean and comfortable, Breakfast is not great. No kitchen. some of the restaurant staff are not friendly

Reviewed on Jun 21, 2026

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Milestone Hotel Deals

Saskatoon Inn

Saskatoon Inn

3.5 out of 5
2002 Airport Drive Saskatoon SK
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $112 total per night from Jun 29 to Jun 30
$112 total
Jun 29 - Jun 30
Total with taxes and fees
8.6/10 Excellent! (6,916 reviews)
"Nice hotel with numerous event capabilities. Good restaurant and bar. Pool looked nice however was closed during my visit. Breakfast was great, included with"

Reviewed on Jun 22, 2026

Saskatoon Inn
Travelodge by Wyndham Saskatoon

Travelodge by Wyndham Saskatoon

2 out of 5
106 Circle Dr W Saskatoon SK
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Jul 1 to Jul 2
$117 total
Jul 1 - Jul 2
Total with taxes and fees
Travelodge by Wyndham Saskatoon
Manitou Springs Resort

Manitou Springs Resort

3.5 out of 5
302 MacLachlan Ave Manitou Beach SK
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Jun 24 to Jun 25
$117 total
Jun 24 - Jun 25
Total with taxes and fees
8.6/10 Excellent! (727 reviews)
"Went for a Family get away to celebrate my elderly parents and Fathers day. The staff at hotel were amazing. They were nice, accomodating and compassionate. Unfortunately our last day at the spa we were greeted by a very unpleasent lady at the front desk of spa. She refused to ever tell me her name. ..."

Reviewed on Jun 22, 2026

Manitou Springs Resort
See all 893 properties in Saskatchewan
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 Milestone Vacation Packages

Milestone Essential Information

Language
English
Currency
Canadian dollars

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Frequently asked questions

How much does a Milestone vacation package cost?
Offering great value package deals from $595 on Expedia, you'll be thrilled with how little a vacation to Milestone costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Milestone?
If you're hoping to book a cheap Milestone vacation package, consider visiting in December, January and February. You'll typically find lower rates on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Milestone?
The ideal duration for your Milestone vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you time to tick off all the top sights and explore some hidden spots along the way.
How to find the best Milestone package deals?
Use Expedia's filter tool to find some unbeatable Milestone package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Milestone package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Milestone vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still get the freedom to create a personalized Milestone vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Milestone?
If you have your Milestone travel dates locked in, book as soon as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for traveling on a whim.
Does Expedia offer Book Now, Pay Later Milestone vacation packages?
If you're anything like us, you love going away but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Milestone break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

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