Windermere Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Windermere Vacation
Art, food, entertainment and more … There's so much to experience with a Windermere vacation package. And with the ability to customize your city getaway, you know it'll be one that's hard to forget. Fill up your itinerary with visits to Oaklawn Farm Zoo, Berwick Heights Golf Course and Valley Drive-In, some of the things you should see during your trip to Windermere. Whoever you're taking a break with and whatever you want to spend, your ultimate Windermere vacation is just clicks away with Expedia.
Top Windermere Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Amsterdam Inn & Suites Sussex
CA $1,277
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Saint John (YSJ)
9.2/10 Wonderful! (953 reviews)
Clean, very welcoming and friendly staff, and excellent breakfast included! Highly recommend and would stay again :)
Reviewed on Sep 28, 2026
Chateau Saint John Trademark Collection by Wyndham
Mount Pleasant
CA $1,485
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Saint John (YSJ)
9.4/10 Exceptional! (1,881 reviews)
The woman serving breakfast at the Château was excellent, friendly, helpful very sweet made our breakfast a wonderful experience. Make sure you let her know so.😊
Reviewed on Sep 27, 2026
Saint John Harbourfront Hotel
Uptown
CA $1,401
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Saint John (YSJ)
8.4/10 Very good! (1,617 reviews)
The breakfast was not great. Staff were amazing. And the pool was beautiful. I give it a 4.5 out of 5. The hotel is also dated. But extremely clean.
Reviewed on Sep 27, 2026
Ready to book your vacation to Windermere?
Windermere Hotel Deals
Old Orchard Inn
153 Greenwich Rd. South Wolfville Ridge NS
Fully refundableReserve now, pay when you stay
CA $208
CA $249 total
Oct 11 - Oct 12
includes taxes & fees
8.6/10 Excellent! (1,033 reviews)
"The room was very dirty. The bed had hairs on it and the floors were do dirty that we did not take our shoes and off."
Reviewed on Sep 27, 2026
Slumber Inn
5534 Prospect Road New Minas NS
Fully refundableReserve now, pay when you stay
CA $199
CA $234 total
Oct 4 - Oct 5
includes taxes & fees
8.8/10 Excellent! (1,029 reviews)
"The pillows are very firm and large, smaller and softer pillows for the beds would be nice. Like as in not so high and firm that your neck has to bend to get up onto the pillow."
Reviewed on Sep 28, 2026
Aurora Inn
831 Main Street Kingston NS
Fully refundableReserve now, pay when you stay
CA $196
CA $223 total
Sep 29 - Sep 30
includes taxes & fees
9/10 Wonderful! (636 reviews)
"Very convenient to walk to restaurants downtown. Easy parking."
Reviewed on Sep 27, 2026
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.
Frequently asked questions
How much does a Windermere vacation package cost?
You can grab a vacation package to this top destination from CA $1,277 on Expedia. However, how much your vacation to Windermere costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Windermere?
To pick up cheap Windermere vacation packages, organize your getaway outside of peak times like public holidays and major festivals. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for Windermere?
Generally, a handful of days is enough to check out the major sights during your Windermere vacation. However, if you'd like to have more time to relax or go on day trips, think about extending your itinerary.
How to find the best Windermere package deals?
Begin your search for a Windermere package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Windermere package deal right away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Windermere escape off to a flying start.
Is it cheaper to book a Windermere vacation as a package?
You can enjoy significant savings on your next Windermere break by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Windermere?
If you have your Windermere travel dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Windermere?
- Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to escape to Windermere.
- Set your budget: Factor in expenses like flights, meals and transportation when working out how much to set aside for your trip to Windermere. Then, select a hotel that suits your budget, whether that's a wallet-friendly stay or a lavish retreat.
- Work out your trip length: Think about how much time you want to spend discovering Windermere. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Windermere vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
