Windermere Vacations from $752

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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.

The Latest Windermere vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Saint John New Brunswick

Days Inn by Wyndham Saint John New Brunswick

2.5 out of 5
Waterloo
Price was $895, price is now $752 per person
$752
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Saint John (YSJ)
8/10 Very Good! (1,592 reviews)
I asked 5 times during booking and same day as reservation for an extra chair in the room. Never happened. we found 3 long black hairs-one in the tub and 2 in the bed. Very disappointed this time.

Reviewed on Nov 23, 2025

Delta Hotels by Marriott Saint John

Delta Hotels by Marriott Saint John

3.5 out of 5
Uptown
Price was $979, price is now $807 per person
$807
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Saint John (YSJ)
8.8/10 Excellent! (1,004 reviews)
Great stay! Definitely coming back. Staff were great and room was clean! No complains 👍

Reviewed on Nov 24, 2025

Chateau Saint John Trademark Collection by Wyndham

Chateau Saint John Trademark Collection by Wyndham

4.5 out of 5
Mount Pleasant
Price was $990, price is now $862 per person
$862
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Saint John (YSJ)
9.6/10 Exceptional! (1,769 reviews)
Lovely room. Very quiet.

Reviewed on Nov 25, 2025

Chipman Hill Suites - Pratt House

Chipman Hill Suites - Pratt House

3.5 out of 5
Uptown
Price was $903, price is now $793 per person
$793
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Saint John (YSJ)
9.4/10 Exceptional! (180 reviews)
Gorgeous, great location, kind staff and felt pampered!

Reviewed on Oct 29, 2025

Rodeway Inn

Rodeway Inn

2 out of 5
Island View
Price was $860, price is now $763 per person
$763
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Saint John (YSJ)
7.4/10 Good! (436 reviews)
The manager Sean couldn't have been more helpful and friendly. A very profesional and a hard worker. Much appreciated suggestions for places to visit on my onward journey to Prince Edward Island. Very good buffet breakfast also. A great place to rest during a long road trip. Thank you! Andrew from Melbourne Australia

Reviewed on Oct 12, 2025

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Private, quiet Valley delight!

Private, quiet Valley delight!

Berwick NS
8/10 Very Good! (6 reviews)
Great Hospitality
House was as advertised. Hot tub and pool were clean and ready to go. Andy put a lot of thought into making the place welcoming and comfortable. Great location to use as a base in exploring Nova Scotia!

Reviewed on Jul 30, 2024

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Private, quiet Valley delight!
Old Orchard Inn

Old Orchard Inn

4 out of 5
153 Greenwich Rd. South Wolfville Ridge NS
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $181 total per night from Nov 30 to Dec 1
$181 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (1,010 reviews)
Staff were super friendly One take away. The ice maker on the second floor has some noise issues

Reviewed on Nov 24, 2025

Old Orchard Inn
Slumber Inn

Slumber Inn

3.5 out of 5
5534 Prospect Road New Minas NS
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $142 total per night from Nov 30 to Dec 1
$142 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
Room was nice but getting dated. Heating/AC was very dated, not a wall thermostat control just a dial on the unit. Shower was very small but well maintained. Room has a fridge, microwave, small closet, desk, two chairs and a small coffee pot. Room could use a luggage rack and some coat hook just ...

Reviewed on Nov 23, 2025

Slumber Inn
See all 113 properties in Windermere
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 the Best Windermere Vacation Packages

Windermere Essential Information

Language
English
Currency
Canadian dollars
Top Sights
Oaklawn Farm Zoo, Paragon Golf and Country Club and Berwick Heights Golf Course

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Frequently asked questions

How much does a Windermere vacation package cost?
You'll find cheap prices from $752 on Expedia for your Windermere escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Windermere costs.
What are the cheapest months to go to Windermere?
December, January and February are the best times to search for cheap Windermere vacation packages. Choosing to travel in quieter periods means you can usually find better prices on flights and hotels.
How many days is enough for Windermere?
Usually, a handful of days is enough to check out the major sights during your Windermere vacation. But if you prefer to have some time to rest or go on day tours, consider extending your itinerary.
How to find the best Windermere package deals?
Use Expedia's handy filters to find some great Windermere package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Windermere package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Windermere vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still get the freedom to create a customized Windermere vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Windermere?
Land amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Windermere adventure.
Does Expedia offer Book Now, Pay Later Windermere vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Windermere vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.