Winchester Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Winchester

Terrace Green Bed & Breakfast

Terrace Green Bed & Breakfast

3 out of 5
11952 County Road 43, North Dundas, ON
Fully refundableReserve now, pay when you stay
The price is S$122 per night from 17 Jul to 18 Jul
S$122
17 Jul - 18 Jul
includes taxes & fees
9.6/10 Exceptional! (103 reviews)
"Well done property - clean and pleasant place"

Reviewed on 19 Jun, 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 S$160 per night from 17 Jul to 18 Jul
S$160
17 Jul - 18 Jul
includes taxes & fees
8.8/10 Excellent! (898 reviews)
"Excellent"

Reviewed on 6 Jul, 2025

Microtel by Wyndham Casselman
SureStay Hotel by Best Western Kemptville

SureStay Hotel by Best Western Kemptville

2.5 out of 5
4022 County Road 43, North Grenville, ON
Fully refundableReserve now, pay when you stay
The price is S$150 per night from 20 Jul to 21 Jul
S$150
20 Jul - 21 Jul
includes taxes & fees
8/10 Very Good! (473 reviews)
"Great!"

Reviewed on 13 Jul, 2025

SureStay Hotel by Best Western Kemptville
See all 51 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.

Frequently asked questions

How much does a Winchester holiday package cost?
You can grab a holiday package to this popular destination on Expedia. But how much your holiday 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 holiday 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 holiday 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday 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 holiday package to Winchester?
If you're planning a spur-of-the-moment Winchester holiday, 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 accommodation, 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 accommodation and airfare: Once you've nailed down your trip dates and duration, book the ideal Winchester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.