Winchester Trips (flight + hotel)

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Top hotels in Winchester

Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

3 out of 5
11952 County Road 43, North Dundas, ON
The price is P4,772 per night from Aug 12 to Aug 13
P4,772
P5,392 total
Aug 12 - Aug 13
includes taxes & fees
9.4/10 Exceptional! (105 reviews)
"Well done property - clean and pleasant place"

Reviewed on Jun 19, 2025

Terrace Green Bed & Breakfast
Microtel by Wyndham Casselman

Microtel by Wyndham Casselman

3 out of 5
17 Rue Industriel, Casselman, ON
Fully refundableReserve now, pay when you stay
The price is P7,112 per night from Aug 17 to Aug 18
P7,112
P8,036 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (945 reviews)
"Overall good."

Reviewed on Aug 9, 2025

Microtel by Wyndham Casselman
McIntosh Country Inn & Conference Centre in Canada

McIntosh Country Inn & Conference Centre in Canada

3.5 out of 5
12495 Highway 2 East, South Dundas, ON
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (403 reviews)
Unexpected Hidden Gem!!!
"McIntosh Country Inn was surprisingly amazing and a real hidden gem. The staff were so friendly and accommodating especially the gentleman that fulfilled my request for a quiet and private space for a meeting in the evening I could not take from my room. Also, the riverfront park and walkways are ..."

Reviewed on Aug 7, 2025

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McIntosh Country Inn & Conference Centre in Canada
See all 49 properties in Winchester
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.

Popular places to visit

Domaine du Cervin

You can enjoy a tasting or tour at Domaine du Cervin during your travels to North Dundas. Make some time to visit the spas while you're in the area.

Domaine du Cervin

Frequently asked questions

How much does a Winchester vacation package cost?
You can grab a vacation package to this popular destination on Expedia. But how much your vacation to Winchester costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Winchester?
Plan your getaway for the off-season and you're likely to score cheap Winchester vacation packages. Remember that public holidays and major events and festivals can impact prices, so do some research before you go.
How many days is enough for Winchester?
The ideal length of your Winchester vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to visit all the top attractions and discover some hidden gems along the way.
How to find the best Winchester package deals?
Landing a cheap Winchester package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Winchester package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights individually. Better still, you can tailor your Winchester 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 Winchester?
If you're planning a spur-of-the-moment Winchester vacation, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your diary and get packing. Your preferred season and the activities available will also help you decide when to escape to Winchester.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should consider other expenses. These include flights, food and transportation. Also, put aside a little extra for unexpected costs that could crop up during your trip to Winchester.
  3. Decide how long to go away for: Now that you're up to speed on Winchester, you can work out the perfect length of your break. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, book the ideal Winchester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.