Orrville 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
Top Orrville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Dudley Inn
CA $1,017
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Muskoka (YQA)
9.8/10 Exceptional! (94 reviews)
We stayed in Room I for one night at this lovely motel. It was absolutely stunning!!
Everything was top notch from the bed to the bathroom fixtures to the decor.
It was our first time checking in by text without seeing an actual person, and it went flawlessly.
Such a great experience.
Reviewed on Sep 23, 2026
Sunnylea Resort
CA $1,097
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Muskoka (YQA)
8.4/10 Very good! (99 reviews)
Cabin was as advertised on-site staff were very helpful and we found the ground on cabin to be extremely clean great value
Reviewed on Sep 19, 2026
Ready to book your vacation to Orrville?
Orrville Hotel Deals
JW Marriott The Rosseau Muskoka Resort & Spa
1050 Paignton House Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
CA $382
CA $491 total
Oct 25 - Oct 26
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Great stay beautiful place"
Reviewed on Sep 24, 2026
Windermere House
2508 Windermere Road Muskoka Lakes ON
CA $293
CA $386 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"The Windermere was as charming and beautiful as you can imagine. We had a wonderful and relaxing stay. The views are incredible, and the staff is so attentive. We loved it so much it’s going to be an annual trip for us. Such a special place"
Reviewed on Sep 24, 2026
Jolly Roger Inn & Resort
2 J.R. Ln Seguin ON
Fully refundableReserve now, pay when you stay
CA $127
CA $144 total
Oct 26 - Oct 27
includes taxes & fees
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 Orrville vacation package cost?
Offering excellent value package deals from CA $931 on Expedia, you'll be thrilled with how little a vacation to Orrville costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Orrville?
You can usually find lower rates and better availability in January, February and November. Browse our cheap Orrville vacation packages and you could land some great off-season discounts.
How many days is enough for Orrville?
Typically, a handful of days is enough to tick off the main attractions during your Orrville vacation. However, if you want to have time to kick back or take day trips, think about extending your itinerary.
How to find the best Orrville package deals?
Begin your search for a Orrville package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Orrville package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Orrville getaway off to a flying start.
Is it cheaper to book a Orrville vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking accommodations and flights separately. Better still, you can personalize your Orrville trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Orrville?
If you have your Orrville vacation dates finalized, book as early as you can to score some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Orrville?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Orrville.
- Work out your budget: Ensure you have enough money to pay for everything from transportation and food to experiences and flights. Your accommodations will probably be the largest expense during your trip to Orrville.
- Decide your trip length: Think about how long you'd like to spend exploring Orrville. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Orrville vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
