Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Winchester Holiday

Our pick of the best Winchester Hotel Deals

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 NZ$158 per night from 17 Aug to 18 Aug
NZ$158
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (106 reviews)
"It was a lovely, warm home to stay in. Next best thing to home! Annette cooked us a lovely breakfast and made sure we knew where to go for dinner."

Reviewed on 13 Aug. 2025

Terrace Green Bed & Breakfast
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

Winchester
The price is NZ$302 per night from 20 Aug to 21 Aug
NZ$302
20 Aug - 21 Aug
includes taxes & fees
10/10 Exceptional! (5 reviews)
"Great spot in Winchester. Everything as promised. Responsive host. Really enjoyed our 7 nights. Cozy spot"

Reviewed on 4 Aug. 2025

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
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 NZ$236 per night from 17 Aug to 18 Aug
NZ$236
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (949 reviews)
"A quick stay close to Calypso waterpark. Clean and accommodating. (A note: We checked in late and most restaurants in town are closed by 8pm.)"

Reviewed on 12 Aug. 2025

Microtel by Wyndham Casselman
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.

What to do in Winchester

Venom Racing Madix | 125cc ATV | Automatic

Guided ATV Wilderness Ride in North Gower

NZ$85
per adult
Guided ATV Wilderness Ride in North Gower
See all activities in Winchester

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.