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Best Comfort Food Restaurants in Charleswood

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17 restaurants available nearby

How are Featured results ranked

A photo of Highwater Bar & Eatery restaurant
1. Highwater Bar & Eatery
4.7
Exceptional(127)
$$$$
• Comfort Food • Winnipeg
Booked 67 times today
Nice cocktail selection. Tasty food. Friendly service. We'll definitely come back
A photo of Cafe Carlo restaurant
2. Cafe Carlo
4.8
Exceptional(2760)
$$$$
• Comfort Food • Little Italy/Corydon Village
Booked 18 times today
Cafe Carlo was amazing !!! We went for our 48th wedding anniversary . The food was so DELICIOUS & the ambiance was great ! My husband had the beef tenderloin with a mushroom Demi glaze, mashed potatoes & broccoli . I had the Vong, fettuccine noodles with baby clams in a garlic wine sauce . Both entrees were terrific ! We shared an apple cherry hazelnut cobbler for dessert . We would definitely return !!!!!
A photo of Kevin's Bistro 1100 Corydon restaurant
3. Kevin's Bistro 1100 Corydon
4.0
Excellent(75)
$$$$
• Comfort Food • Winnipeg
Booked 10 times today
First visit and it didn’t disappoint! Ambiance is lovely. Food was very good and service was great. We will be back!
A photo of Kevin's Bistro restaurant
4. Kevin's Bistro
4.3
Awesome(589)
$$$$
• Comfort Food • Exchange District
Booked 17 times today
Very attentive service, Mac & cheese (Opus) was delicious, spicy potato tomato soup was very tasty and Caesar salad was crisp and tangy. Desserts from Stella’s are a great addition.
A photo of James Avenue Pumphouse restaurant
5. James Avenue Pumphouse
4.7
Exceptional(1201)
$$$$
• Comfort Food • Winnipeg
Booked 43 times today
Great food and service! It's such a cool building inside and out as well!
A photo of Peasant Cookery restaurant
6. Peasant Cookery
4.6
Exceptional(1659)
$$$$
• Comfort Food • Exchange District
Booked 14 times today
Excellent food, great service and a wonderful time
A photo of Olive Garden Italian Restaurant - Winnipeg Polo Park restaurant
7. Olive Garden Italian Restaurant - Winnipeg Polo Park
4.5
Awesome(111)
$$$$
• Comfort Food • Winnipeg
Booked 48 times today
Jennifer and Nate were excellent servers and always attentive to our needs. Everything was on time, from Drinks to meals.
A photo of Montana's BBQ & Bar - Winnipeg - Sterling Lyon restaurant
8. Montana's BBQ & Bar - Winnipeg - Sterling Lyon
4.0
Excellent(0)
$$$$
• Comfort Food • Winnipeg
Montana's BBQ & BAR is a Canadian comfort food BBQ restaurant and sports bar. Enjoy in-house smoked pork ribs, beef brisket, grilled steaks and juicy burgers which are paired perfectly with catching the game. Montana's Winnipeg celebrates fun-to-eat, finger-licking smoked and barbecued comfort food that breaks the 'proper' rules. Located near Eric Coy Arena & Assiniboine Park Zoo in the Southern end of Winnpeg. Experience the fun, casual and unpretentious vibe, where you can laugh heartily, enjoy classic BBQ cooking, cheer on the game and enjoy your friends and family. We can't wait to serve you at our restaurant.
A photo of Next Door restaurant
9. Next Door
4.7
Exceptional(130)
$$$$
• Comfort Food • Winnipeg
Booked 13 times today
Killer burger and fries paired with a Hazy IPA…amazing way to end the day!
A photo of Montana's BBQ & Bar - Winnipeg - Polo Park restaurant
10. Montana's BBQ & Bar - Winnipeg - Polo Park
4.1
Excellent(24)
$$$$
• Comfort Food • Winnipeg
Booked 4 times today
Our party was a family with 2 children. The kids had several good kid friendly options to choose from and were happy with the menu. The portion sizes on all our meals were large. Our appetizer was spinach dip with pitas and chips - very delicious, I would say the food was good overall but not exceptional. The prices were reasonable and it was a good choice for a family restaurant. The many screens were somewhat of a distractions for the kids but that is common in lots of restaurants.

See what locals rave about

From verified diners like you
From verified diners like you
  • Jarett Cindy
    Minneapolis - St. Paul •1 review
    5.0
    Dined 2 days ago
    Jennifer and Nate were excellent servers and always attentive to our needs. Everything was on time, from Drinks to meals.
    More info
    Olive Garden Italian Restaurant - Winnipeg Polo Park$$$$• Italian• Winnipeg
    •
    4.5
  • Kevin and Deborah
    Winnipeg / Manitoba •3 reviews
    5.0
    Dined on Oct 27, 2026
    Cafe Carlo was amazing !!! We went for our 48th wedding anniversary . The food was so DELICIOUS & the ambiance was great ! My husband had the beef tenderloin with a mushroom Demi glaze, mashed potatoes & broccoli . I had the Vong, fettuccine noodles with baby clams in a garlic wine sauce . Both entrees were terrific ! We shared an apple cherry hazelnut cobbler for dessert . We would definitely return !!!!!
    More info
    Cafe Carlo$$$$• Italian• Little Italy/Corydon Village
    •
    4.8
  • Melanie
    Winnipeg / Manitoba •2 reviews
    5.0
    Dined on Oct 26, 2026
    We had a really lovely experience here for my daughter's birthday. The atmosphere and the service were great and the food was delicious. And they were able to accommodate a last minute change in our reservation.
    More info
    Kevin's Bistro 1100 Corydon$$$$• Bistro• Winnipeg
    •
    4
  • Emmanuel
    Winnipeg / Manitoba •1 review
    5.0
    Dined on Oct 9, 2026
    Sophia was very outstanding with her service and attention to customer needs Had a Beautiful experience with the kids party
    More info
    The Rec Room - Winnipeg Seasons of Tuxedo$$$$• Contemporary Canadian• Southwest Winnipeg
    •
    4.7
  • Lorraine
    Winnipeg / Manitoba •11 reviews
    4.0
    Dined on Sep 3, 2026
    Our party was a family with 2 children. The kids had several good kid friendly options to choose from and were happy with the menu. The portion sizes on all our meals were large. Our appetizer was spinach dip with pitas and chips - very delicious, I would say the food was good overall but not exceptional. The prices were reasonable and it was a good choice for a family restaurant. The many screens were somewhat of a distractions for the kids but that is common in lots of restaurants.
    More info
    Montana's BBQ & Bar - Winnipeg - Polo Park$$$$• Barbecue• Winnipeg
    •
    4.1

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