Windermere Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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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.
Kennedy House
Price was CA $457, price is now CA $377 per person
CA $377
per person
Oct 10 - Oct 13
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Saint John (YSJ)
8.8/10 Excellent! (871 reviews)
We liked the location and how it was so close to everything on Main Street. We were very disappointed with our check-in. The gentleman ( that wears a hat) was not a bit welcoming and acted like we were a nuisance to him. He was very short with us when we checked in. We did have a chance to speak to the owner of the hotel at one point during our stay. He was very friendly and we had a great chat with him about the history of his hotel and upcoming renovations.
Reviewed on Sep 9, 2025
Homeport Suites & Residences
Price was CA $620, price is now CA $475 per person
CA $475
per person
Oct 10 - Oct 13
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Saint John (YSJ)
9/10 Wonderful! (25 reviews)
Loved the cleanliness of the room and restaurant. The staff was very helpful and pleasant. Loved having the restaurant and a gift shop in the same building. I would suggest a grab bar outside the shower/tub and availability of ice on the floor.
Reviewed on Sep 5, 2025
Mamas by the sea B&B
Price was CA $635, price is now CA $508 per person
CA $508
per person
Oct 10 - Oct 14
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Saint John (YSJ)
10/10 Exceptional! (114 reviews)
This was a very tiny well-kept and clean facility with in a 15 minute drive 5 of the most beautiful beaches I have ever seen for more Nova Scotia staycation 2025
Reviewed on Sep 1, 2025
Windermere Hotel Deals
Old Orchard Inn
153 Greenwich Rd. South, Exit 11, Highway 101, Wolfville Ridge, NS
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Oct 2 to Oct 3
CA $219
CA $262 total
Oct 2 - Oct 3
includes taxes & fees
Micro Boutique Living Wolfville
336 Main Street, Wolfville, NS
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
