Winchester Vacations from ￥313,915

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to ￥45,448 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

The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
SOHO Residences Champagne

SOHO Residences Champagne

4 out of 5
Centretown West
per person
Aug 9 - Aug 14
found 14 hours ago
Roundtrip flight included
Osaka (KIX) to Ottawa (YOW)
9.2/10 Wonderful! (389 reviews)
Decent stay, but not as expected. Location was nice and within walking distance to Little Italy, which was lovely. However, the Concierge never did answer any of my phone calls during my stay and general interactions could have been friendlier (I suggest being prepared to state that you are there for a short term stay and in which room before they abruptly ask, "Who are you?" so it doesn't catch you off guard). I'd ask to avoid a mezzanine level booking if possible (we were assigned this and it was a bit disappointing). Room was very hot for the duration of our stay despite adjusting the thermostat, drinking glasses were chipped and not very clean, and maintenance work started just before 0730am above our room which was not anticipated nor were we informed about it. Generally, it was a decent place to put our heads down as we were out for much of the day but for the amount paid, I would definitely consider other options.

Reviewed on Jun 9, 2025

reStays Ottawa

reStays Ottawa

4 out of 5
Downtown Ottawa
per person
Aug 9 - Aug 14
found 14 hours ago
Roundtrip flight included
Osaka (KIX) to Ottawa (YOW)
9.6/10 Exceptional! (1,423 reviews)
Fabulous! Clean, front desk staff were amazing.

Reviewed on Jun 24, 2025

Le Germain Hotel Ottawa

Le Germain Hotel Ottawa

4 out of 5
Downtown Ottawa
per person
Aug 9 - Aug 14
found 14 hours ago
Roundtrip flight included
Osaka (KIX) to Ottawa (YOW)
9.4/10 Exceptional! (1,000 reviews)
A truly lovely experience.

Reviewed on Jun 20, 2025

Cartier Place Suite Hotel

Cartier Place Suite Hotel

3 out of 5
Centretown
per person
Aug 9 - Aug 14
found 14 hours ago
Roundtrip flight included
Osaka (KIX) to Ottawa (YOW)
8.2/10 Very Good! (3,721 reviews)
I loved everything about it i really enjoyed my stay there

Reviewed on Jun 23, 2025

SOHO Residences Lisgar

SOHO Residences Lisgar

4 out of 5
Centretown
per person
Aug 9 - Aug 14
found 14 hours ago
Roundtrip flight included
Osaka (KIX) to Ottawa (YOW)
9.4/10 Exceptional! (390 reviews)
Easy check in, great space, location was good

Reviewed on Jun 14, 2025

Find the Best Winchester Vacation Packages

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 ￥12,220 per night from Jun 25 to Jun 26
￥12,220
￥13,809 total
Jun 25 - Jun 26
includes taxes & fees
9.6/10 Exceptional! (103 reviews)
"Well done property - clean and pleasant place"

Reviewed on Jun 19, 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 ￥14,059 per night from Jul 2 to Jul 3
￥14,059
￥25,133 total
Jul 2 - Jul 3
includes taxes & fees
10/10 Exceptional! (3 reviews)
Nice place
"How is very well designed and equipped, full of nice details. Location cannot be better. Communication has been great and listing accurate. Highly recommended!"

Reviewed on May 17, 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 ￥16,710 per night from Jun 26 to Jun 27
￥16,710
￥18,882 total
Jun 26 - Jun 27
includes taxes & fees
8.8/10 Excellent! (880 reviews)
"Great Hotel"

Reviewed on Jun 20, 2025

Microtel by Wyndham Casselman
See all 50 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 vacation package cost?
You can grab a vacation package to this popular destination from ￥313,915 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.