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Hotels in Headingley

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Choose from 511 Headingley Hotel Deals

Best Western Plus Winnipeg West

Best Western Plus Winnipeg West

2.5 out of 5
4140 Portage Avenue, Headingley, MB
  • 28 min walk from John Blumberg Softball Complex
Book a stay at this eco-certified hotel in Headingley. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,017 reviews)
"Close to the golf course"

Reviewed on Jul 24, 2025

Best Western Plus Winnipeg West
Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue, Hwy 101 North, Headingley, MB
  • 11 min walk from John Blumberg Softball Complex
Stay at this motel in Headingley. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (1,125 reviews)
"Excellent pet-friendly option on our way to Ottawa from Calgary. And with easy access to green space -- including a little fenced dog park for the four-legged. Four paws up!"

Reviewed on Jul 29, 2025

Motel 6 Headingley, MB - Winnipeg West
Birchwood Inn, BW Premier Collection

Birchwood Inn, BW Premier Collection

3 out of 5
2520 Portage Ave, Winnipeg, MB
  • 16 min drive from John Blumberg Softball Complex
Stay at this 3-star business-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
8.6/10 Excellent! (1,222 reviews)
"Beds were comfortable which always makes me happy. Hotel was very clean, staff and amenities were great."

Reviewed on Aug 1, 2025

Birchwood Inn, BW Premier Collection
Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
1808 Wellington Ave, Winnipeg, MB
  • 24 min drive from John Blumberg Softball Complex
Book a stay at this family-friendly hotel in Winnipeg. Enjoy free WiFi, free water park access, and breakfast (surcharge). Our guests praise the pool and the ...
8.4/10 Very Good! (2,169 reviews)
"Super friendly staff at front desk. Check in went well. Hotel looks brand new. Room looks new and modern also. Only complaint is there was hair kind of allover the bathroom like it was “cleaned” very quickly"

Reviewed on Aug 2, 2025

Victoria Inn Hotel and Convention Centre Winnipeg
The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection

The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection

4 out of 5
222 Broadway, Winnipeg, MB
  • 35 min drive from John Blumberg Softball Complex
Book a stay at this spa hotel in Winnipeg. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9/10 Wonderful! (1,006 reviews)
Beautiful hotel but…
"The hotel was beautiful and staff nice but we were out in a room that must have been above the speakers in a ballroom with either a bar mitzvah or wedding going on until after midnight. We could even tell What song they were playing! Beds are ok but not the most comfy. The common spaces are quite ..."

Reviewed on Aug 2, 2025

The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection
Lakeview Signature, Trademark Collection by Wyndham

Lakeview Signature, Trademark Collection by Wyndham

3 out of 5
1999 Wellington Ave, Winnipeg, MB
  • 22 min drive from John Blumberg Softball Complex
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.8/10 Excellent! (2,247 reviews)
"Excellent position, close to the airport" Excellent"

Reviewed on Aug 2, 2025

Lakeview Signature, Trademark Collection by Wyndham
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
260 Main Street, Winnipeg, MB
  • 35 min drive from John Blumberg Softball Complex
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,304 reviews)
"I likw it"

Reviewed on Jul 29, 2025

Humphry Inn & Suites
Alt Hotel Winnipeg

Alt Hotel Winnipeg

3 out of 5
310 Donald Street, Winnipeg, MB
  • 34 min drive from John Blumberg Softball Complex
Stay at this 3-star eco-certified hotel in Winnipeg. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,045 reviews)
"Great hotel, but wouldn't want to walk in streets around the area after dark. During the day many drunk/drugged individuals asked us for money. Was warned by someone to hold onto our bags as could be snatched. Like other city centres, both shopping malls were devoid of shops. A great pity as hotel ..."

Reviewed on Aug 1, 2025

Alt Hotel Winnipeg
Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
826 Regent Avenue West, Winnipeg, MB
  • 52 min drive from John Blumberg Softball Complex
Stay at this 3-star eco-certified hotel in Winnipeg. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the helpful staff in our ...
8/10 Very Good! (1,000 reviews)
"Friendly staff, clean room"

Reviewed on Jul 31, 2025

Canad Inns Destination Centre Transcona
Mere Hotel

Mere Hotel

3.5 out of 5
333 Waterfront Drive, Winnipeg, MB
  • 36 min drive from John Blumberg Softball Complex
Stay at this 3.5-star business-friendly hotel in Winnipeg. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful ...
8.8/10 Excellent! (1,086 reviews)
"Awesome"

Reviewed on Aug 3, 2025

Mere Hotel
Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
1415 Regent Ave W, Winnipeg, MB
  • 49 min drive from John Blumberg Softball Complex
Stay at this 3-star eco-certified hotel in Winnipeg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,241 reviews)
"Had a great experience there, room was very clean, check in very fast, comfortable bed, staff was courteous and helpful"

Reviewed on Jul 31, 2025

Canad Inns Destination Centre Club Regent Casino Hotel
Travelodge by Wyndham Winnipeg East

Travelodge by Wyndham Winnipeg East

2 out of 5
20 Alpine Ave, St Annes Road, Winnipeg, MB
  • 40 min drive from John Blumberg Softball Complex
Book a stay at this eco-certified hotel in Winnipeg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
8/10 Very Good! (1,476 reviews)
"Breakfast was good."

Reviewed on Aug 2, 2025

Travelodge by Wyndham Winnipeg East
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 cheap hotels in Headingley

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Frequently Asked Questions About Headingley hotels

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How many hotels are there in Headingley?

With over 511 hotels in Headingley, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $96.

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