Deals on vacations and trips to Winkler

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Winkler flight + hotel vacation packages

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

Canad Inns Destination Centre Garden City

3 out of 5
Leila-McPhillips Triangle
Price was $998, price is now $867 per person
$867
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
This smoke-free hotel features free water park access, a nightclub, and a restaurant. Bring the family and enjoy the children's pool, waterslide, and kid-friendly dining. Enjoy the indoor pool and perks like free self parking and free WiFi.
Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $1,105, price is now $923 per person
$923
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Bring the family and enjoy the free kid's club, children's pool, and kid-friendly dining. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $1,173, price is now $992 per person
$992
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast and free WiFi. Traveling for business? Take advantage of the business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
Canad Inns Destination Centre Windsor Park

Canad Inns Destination Centre Windsor Park

3 out of 5
Windsor Park
Price was $1,039, price is now $912 per person
$912
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a gym. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.
Sandman Signature Winnipeg Airport Hotel & Suites

Sandman Signature Winnipeg Airport Hotel & Suites

4 out of 5
St. James
Price was $1,201, price is now $1,069 per person
$1,069
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free airport shuttle. Enjoy the hot tub and perks like free self parking.

Top Winkler hotels deals

Days Inn & Suites by Wyndham Winkler

Days Inn & Suites by Wyndham Winkler

2.5 out of 5
395 Boundary Trail Winkler MB
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $96 total per night
$96 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Best Western Plus Winkler

Best Western Plus Winkler

2.5 out of 5
1705 Diamond Dr Winkler MB
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $118 total per night
$118 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a snack bar/deli, and express check-out are also offered.
Pool
Breakfast included
Studio 7 – Mighty, Modern, Fully Equipped

Studio 7 – Mighty, Modern, Fully Equipped

Winkler MB
$90 nightly
The price is $101 total per night
$101 total
Oct 19 - Oct 20
Total with taxes and fees
Stay at this apartment in Winkler. Enjoy air conditioning. Popular attractions Valley Bowling Lanes and Winkler Aquatic Centre are located nearby.
Kitchen
Air conditioning
Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
851 Main Street Winkler MB
Get rates
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Enjoy the 24-hour gym and free perks like full breakfast and free self parking.
Pool
Hot Tub
Pine Loft. Quiet place in the Winkler/Morden area and just off Highway 14.

Pine Loft. Quiet place in the Winkler/Morden area and just off Highway 14.

Winkler MB
Get rates
This vacation home features laundry facilities.
Kitchen
Washer
Best Western Plus Morden

Best Western Plus Morden

2.5 out of 5
253 Loren Dr Morden MB
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $110 total per night
$110 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.
Pool
Hot Tub
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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.

Stay near popular Winkler attractions

PW Enns Centennial Concert Hall

6.4/10 (5 reviews)
You can enjoy a show at PW Enns Centennial Concert Hall during your trip to Winkler. Discover the stargazing spots while you're in the area.
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Frequently asked questions

How much are vacation packages to Winkler?
You can land a great flight and hotel bundle for a mere $867. With one of our Travelocity vacation packages, a getaway to Winkler has never looked more enticing! Save both time and cash and then get a start on packing those bags.
How long should my Winkler vacation be?
Generally, people spend 2 nights in Winkler. Although, that might not be sufficient time for you. If you aim to discover some of the region's off-the-beaten-path gems, why not add another few nights to your travel itinerary?
Where can I get the best vacation package deals for Winkler?
You'll discover an excellent range of Winkler package deals on Travelocity. With 400 partner airlines and 1,000,000 properties across the globe, putting together your ideal escape won't take long.
Why should I book my Winkler vacation package via Travelocity?
Because you'll never wander alone if you book with us, and we offer round-the-clock customer support and top-quality service to boot. Add to that our Price Match Guarantee and a massive range of destinations and experiences to select from. It's our job to help you have the vacation of a lifetime.
Can I save on my Winkler car rental if I bundle it with hotels and flights?
You can with our Winkler vacation packages. With one of these, there are plenty of ways to stretch your budget further. Bundle any two or more car, flight, hotel and tour bookings and watch your savings pile up. With a rental car, all the landmarks around Winkler are a fun road trip away.
What is there to do in Winkler?
There's a certain magic as you wander through the streets of Winkler. Winkler Aquatic Centre and PW Enns Centennial Concert Hall are just a couple of landmarks that make this city so popular, so put them at the top of your travel itinerary.
Where should I stay when visiting Winkler?
If you're looking for somewhere to spend your nights, take a look at the Days Inn & Suites by Wyndham Winkler. It's the top choice for many travelers.

Photos of local treasures

Browse Winkler vacation photos for more inspiration

A field with hay bales and a forest with autumn-colored trees.
Two colorful beehive stacks in a field with yellow flowers.