36+ Vacation Rentals & Holiday Homes in Headingley |
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Headingley Accommodations - Hotels & Rentals

About Headingley Vacation Rentals

Discover More than 36 Incredible Getaway Rentals Available in Headingley. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Headingley.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Headingley, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Headingley. The Average Size of Places to Stay Near Headingley is 488.55 ft², with Prices Averaging US $169 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Headingley. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Headingley

Type Count
Vacation Homes 18
Holiday Apartments 2
Villas 1

Use these Quick Filters to Find a Vacation Rental in Headingley

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Headingley with Online Reservations.

Weather in Headingley, MB

View the weather forecast for Headingley before booking your Headingley Vacation Rentals to confirm your best time to go.

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Activities HeadingleyGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World HeadingleyGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


John Blumberg Softball Complex
BellMTS Iceplex
Red River Exhibition Park
John Blumberg Golf Course
Thunder Rapids Fun Park
Bell MTS Place
Polo Park
University of Manitoba
RBC Convention Centre Winnipeg
Health Sciences Centre
St. Boniface Hospital
Assiniboine Park Zoo
Forks Market
University of Winnipeg
Outlet Collection Winnipeg
Club Regent Casino
Canadian Museum for Human Rights
McPhillips Station Casino
Red River College
St. Vital Centre

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Thunder Rapids Fun Park 45 Properties
Red River Exhibition Park 38 Properties
BellMTS Iceplex 34 Properties
John Blumberg Softball Complex 30 Properties
John Blumberg Golf Course 28 Properties

Frequently Asked Questions About Headingley?

What are the top hotels, lake houses & vacation rentals in Headingley?

We provide an array of great vacation destinations in Headingley. If you are looking to stay in or around the Headingley area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Headingley:

Which hotel, lake house, or vacation rental in Headingley is best for families?

Searching for a family-friendly getaway in Headingley? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Headingley?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 36 in the Headingley area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Headingley.


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