Winchester Vacations from $411

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The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites - Gatineau - Ottawa by IHG

Holiday Inn Express & Suites - Gatineau - Ottawa by IHG

2.5 out of 5
Price was $466, price is now $411 per person
$411
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ottawa (YOW)
8.8/10 Excellent! (1,684 reviews)

Homewood Suites by Hilton Ottawa Kanata

Homewood Suites by Hilton Ottawa Kanata

3 out of 5
Kanata
Price was $886, price is now $751 per person
$751
per person
Dec 28 - Jan 2
just found
Roundtrip non-stop flight included
Nashville (BNA) to Ottawa (YOW)
9.4/10 Exceptional! (1,033 reviews)
Very clean property, helpful staff. Would definitely stay here again!

Reviewed on Oct 26, 2026

Wingate by Wyndham Kanata West Ottawa

Wingate by Wyndham Kanata West Ottawa

3 out of 5
West Carleton
Price was $977, price is now $835 per person
$835
per person
Dec 28 - Jan 2
found 1 hour ago
Roundtrip non-stop flight included
Nashville (BNA) to Ottawa (YOW)
9.2/10 Wonderful! (2,177 reviews)

Fairmont Chateau Laurier

Fairmont Chateau Laurier

5 out of 5
Downtown Ottawa
Price was $579, price is now $495 per person
$495
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ottawa (YOW)
8.8/10 Excellent! (4,023 reviews)
Traffic in Ottawa rush hour can be troublesome, but from the time the valet took the car, until checking out, my stay was dreamlike.

Reviewed on Oct 27, 2026

Holiday Inn Express & Suites Ottawa West - Nepean by IHG

Holiday Inn Express & Suites Ottawa West - Nepean by IHG

2.5 out of 5
Nepean
Price was $549, price is now $491 per person
$491
per person
Jan 7 - Jan 10
found 13 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ottawa (YOW)
8.8/10 Excellent! (1,278 reviews)
Loved the room, king bed and the hot tub were just what we needed. They are going to be doing a major reno soon, check that out before you stay there.

Reviewed on Oct 26, 2026

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Winchester Hotel Deals

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

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

Winchester ON
10/10 Exceptional! (6 reviews)
"It was a great place to stay, we will be back!!!"

Reviewed on Nov 22, 2025

Get rates
RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa
Hard Rock Hotel & Casino Ottawa

Hard Rock Hotel & Casino Ottawa

4.5 out of 5
4837 Albion Road South Ottawa ON
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $190 total per night from Nov 3 to Nov 4
$190 total
Nov 3 - Nov 4
Total with taxes and fees
Hard Rock Hotel & Casino Ottawa
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
$128 nightly
The price is $144 total per night from Nov 6 to Nov 7
$144 total
Nov 6 - Nov 7
Total with taxes and fees
McIntosh Country Inn & Conference Centre in Canada
See all 44 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.

Find the Best Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Macdonald-Cartier Intl. Airport (YOW)
Population
2,400
Max Temp Winter
25ºF
Max Temp Summer
75ºF

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Frequently asked questions

Is Winchester better suited for a beach vacation or a cultural trip?
Winchester is a central urban destination known for family-friendly attractions, offering access to outdoor activities like Iroquois Beach, about 9 miles from central Winchester, for those seeking a lakeside experience.

For entertainment, Calypso Water Park is about 17 miles from central Winchester, providing a fun option for families. This blend makes a Winchester vacation appealing for those looking for a mix of urban convenience and outdoor fun.
How can I save money on a Winchester vacation package?
When you bundle, you can save up to 30%*. To save money on a Winchester package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Winchester?
A Winchester vacation offers family-friendly attractions and outdoor recreation:

Browse and book things to do in Winchester on Expedia.
Can I change or cancel my Winchester vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Winchester vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winchester vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Winchester?
To find last-minute vacation packages to Winchester, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Winchester vacation packages?
Free cancellation on a Winchester vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Winchester vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Winchester getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Winchester vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

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