Title: City of Winchester Vacation Packages & Trips 2025 from CA $1,349 | Expedia.ca

 

[City of Winchester Hotels](https://expedia.ca/Destinations-In-City-Of-Winchester.d553248635976006030.Hotel-Destinations)[Vacation Rentals in City of Winchester](https://expedia.ca/Destinations-In-City-Of-Winchester.d553248635976006030.Vacation-Rental-Destinations)[City of Winchester Car Rentals](https://expedia.ca/Destinations-In-City-Of-Winchester.d553248635976006030.Car-Rental-Destinations)

![](https://images.trvl-media.com/place/6092087/b5336a81-f8cd-4816-a21d-c5f9dafe09ab.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# City of Winchester Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

-   ## 
    
    Plan, book, travel with confidence
    
-   ### 
    
    Better together
    
    Save up to CA $1,096 when you book a flight and hotel together\*
    
-   ### 
    
    Find the right fit
    
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    
-   ### 
    
    Rest easy
    
    Plan, book, and manage your trip all in one place
    

### Your City of Winchester Vacation

With a City of Winchester vacation package, you can forget about planning stresses and put all your energy into experiencing what this lively destination has to offer. You can expect to have a must-visit list as long as your arm during your trip to City of Winchester. One top city you'll want to explore is [Winchester](https://www.expedia.ca/Winchester.d5477.Destination-Travel-Guides). If you're ready to stop dreaming and start packing, Expedia will help turn your City of Winchester vacation into a reality.

## Top vacation destinations in City of Winchester

![Southampton which includes château or palace, heritage elements and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/58000/58882-Southampton.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Southampton

[](https://expedia.ca/Southampton.d3245.Destination-Travel-Guides)

![Winchester featuring heritage architecture and a fountain](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/126000/126817-Winchester.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Winchester

[](https://expedia.ca/Winchester.d5477.Destination-Travel-Guides)

## Top City of Winchester Vacation Deals

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

![Hampshire Court Hotel & Spa](https://images.trvl-media.com/lodging/1000000/440000/430200/430158/26a61393_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampshire Court Hotel & Spa

CA $1,349

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

8/10 Very Good! (565 reviews)

We had such a lovely time here, very chilled and relaxed, we loved the relaxation room.. breakfast was wonderful everything you could want, nice atmosphere too.. room was tidy and clean,bed was super comfy too..thank you for making our stay so enjoyable 👍

Reviewed on Nov 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-18/?FromAirport=YYZ&Destination=SOU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=430158&paandie=true&dealMarker=G5hR2WZxIDiPnKQRgnGP8Z21_lf9wuinhxiwYG7rYBwqQLexMzlTKHQWMatUBipk)

![No.4 Carlton Hotel](https://images.trvl-media.com/lodging/92000000/91410000/91400200/91400160/cf9412b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### No.4 Carlton Hotel

The Polygon

CA $3,834

per person

Jan 14 - Jan 15

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Southampton (SOU)

9.6/10 Exceptional! (122 reviews)

Decor, hotel quality, and cleanliness was excellent. Lots of great amenities included. Guest service was friendly and efficient. Important to note that there is no elevator. Also, glassed in bathroom was not very private and sound through ceiling and room door was very noticeable.

Reviewed on Oct 23, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-14/2026-01-15/?FromAirport=TYO&Destination=SOU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=91400160&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxce_8wEZbRxIUhCDHYKAMt0bNla0h6QT080d2hFeKiwiu)

![Leonardo Hotel Southampton ](https://images.trvl-media.com/lodging/2000000/1180000/1178300/1178290/0c96afed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Leonardo Hotel Southampton

The Polygon

CA $3,657

per person

Jan 14 - Jan 15

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Southampton (SOU)

8.4/10 Very Good! (1,200 reviews)

Good location, friendly staff, good buffet breakfast

Reviewed on Nov 6, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-14/2026-01-15/?FromAirport=TYO&Destination=SOU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1178290&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxce_8wEZbRxIUhCDHYKAMt0auJyx2Ug4HOj9qJj1aW70X)

![Rhinefield House Hotel](https://images.trvl-media.com/lodging/1000000/490000/486300/486289/773e6268_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Rhinefield House Hotel

CA $3,761

per person

Jan 14 - Jan 15

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Southampton (SOU)

8.8/10 Excellent! (651 reviews)

Excellent location, walking distance to the Giant Tree alley. Breakfast was 5 star level - very very nice.

Reviewed on Oct 25, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-14/2026-01-15/?FromAirport=TYO&Destination=SOU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=486289&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxce_8wEZbRxIUhCDHYKAMt0b7dQOQYWLfgxX2WX5os2VU)

![Winchester Wessex Hotel by Sunday](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/3ac6caac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Winchester Wessex Hotel by Sunday

CA $3,681

per person

Jan 14 - Jan 15

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Southampton (SOU)

7.4/10 Good! (1,008 reviews)

The room was fine with a nice view of the Cathedral but showed considerable signs of wear and tear. The bathroom had a cracked basin, a toilet that wouldn't flush properly and a bath that hadn't been cleaned. We advised reception about the bath when we arrived, they promised to sort it the next day, but it was still dirty 2 days later when we left. Breakfast was fine (but definitely not free) and we enjoyed the location in the centre of Winchester.

Reviewed on Nov 5, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-14/2026-01-15/?FromAirport=TYO&Destination=SOU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4799&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxce_8wEZbRxIUhCDHYKAMt0YsdDDngglAgTnGpbHDTZGc)

## City of Winchester Hotel Deals

![The Winchester Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/26100/26080/4127003a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Winchester Hotel & Spa

Worthy Lane, Winchester, England

Fully refundableReserve now, pay when you stay

CA $141

CA $169 total

Nov 13 - Nov 14

includes taxes & fees

8.4/10 Very Good! (1,005 reviews)

Very good hotel. All very clean. Didn’t get my drinks vouchers which was disappointing.

Reviewed on Nov 1, 2025

[](https://expedia.ca/Hotel-Search?startDate=13%2F11%2F2025&endDate=14%2F11%2F2025&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true&regionId=553248635976006030)

![Meon Valley Hotel, Golf & Country Club](https://images.trvl-media.com/lodging/1000000/50000/47800/47731/0e19fdb3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Meon Valley Hotel, Golf & Country Club

Sandy Lane, Shedfield, Southampton, England

Fully refundableReserve now, pay when you stay

CA $75

CA $91 total

Nov 23 - Nov 24

includes taxes & fees

6.8/10 (1,003 reviews)

I read the reviews after booking and to be honest I was not expecting much, but it was lovely. Room spacious and clean, bathroom clean and well stocked. Lots of tea and coffee in room, along with biscuits. Are in the hotel, excellent hot food!!

Reviewed on Oct 19, 2025

[](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=47731&PinnedHotelID=47731&HadPinnedHotel=true&regionId=553248635976006030)

![New Place](https://images.trvl-media.com/lodging/2000000/1590000/1587200/1587150/3b94f834_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

New Place

Shirrell Heath, Southampton, England

Fully refundableReserve now, pay when you stay

CA $88

CA $105 total

Dec 7 - Dec 8

includes taxes & fees

8.4/10 Very Good! (1,003 reviews)

Relax and enjoy the ambiance!

Reviewed on Oct 29, 2025

[](https://expedia.ca/Hotel-Search?startDate=07%2F12%2F2025&endDate=08%2F12%2F2025&selected=1587150&PinnedHotelID=1587150&HadPinnedHotel=true&regionId=553248635976006030)

[See all 5,672 properties in City of Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&regionId=553248635976006030)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a City of Winchester vacation package cost?

> Custom build your City of Winchester package from just CA $1,349. Choose from any combination of flights, hotels and rental cars to craft the escape you've been dreaming of. Remember to add on a few experiences or activities!

### How do I get a cheap travel package to City of Winchester?

> Our City of Winchester vacation packages offer plenty of savings for the savvy explorer. For the best deal, simply combine your flights, hotels and extras (including activities) into a handy package. But cheap prices are just the beginning of your next memorable adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels around the globe to pick from. Whatever your budget or style, there's a package here just for you.

### Where should I stay in City of Winchester?

> If you're eager to see popular sights such as Winchester Cathedral and Great Hall, head straight for [Winchester](https://www.expedia.ca/Winchester.d5477.Destination-Travel-Guides). You might want to stay a while to fully experience this buzzing city.

### What are the top hotels in City of Winchester?

> When it comes to properties in Winchester, [Winchester Royal Hotel](https://www.expedia.ca/Winchester-Hotels-Winchester-Royal-Hotel.h18535.Hotel-Information) and [Mercure Wessex Winchester Hotel](https://www.expedia.ca/Winchester-Hotels-Mercure-Wessex-Winchester-Hotel.h4799.Hotel-Information) are two fantastic options. If you're visiting Fareham, [Moxy Southampton](https://www.expedia.ca/Southampton-Hotels-Moxy-By-Marriott-Southampton.h42101688.Hotel-Information) and [Leonardo Hotel Southampton - Formerly Jurys Inn](https://www.expedia.ca/Southampton-Hotels-Jurys-Inn-Southampton.h1178290.Hotel-Information) will make you feel at home.

### How far in advance should I book my City of Winchester vacation?

> Travelers can normally compare international fares on Expedia within 12 months of departure. Booking late? With a little bit of luck, it's still possible to score an affordable ticket just weeks before your flight.

### What does an Expedia City of Winchester travel package include?

> From airfares and hotels to car rentals, Expedia can help you craft a City of Winchester package that suits you. Vacationing for a week or two? Look into a flight, rental car and hotel bundle. If you can only manage a quick getaway, a flight and hotel deal may be more your style. Activities can also be added once you've made your booking. Our vacation packages make it easy to save and plan.

### What should I know before booking a City of Winchester travel package?

> Whether it's adventure or relaxation you're seeking, a City of Winchester vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the more you'll save!

### Can I choose my airline with a City of Winchester Expedia vacation package?

> Expedia offers access to more than 550 airline partners globally, so you definitely can. Just pick the carrier that suits you and craft your ideal City of Winchester escape.

### If I'm not able to travel, can I cancel my City of Winchester vacation package?

> We totally get it — sometimes life doesn't go according to plan. If you've booked a City of Winchester vacation package and have to cancel or change it, we can help. We recommend browsing our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) first for information. But in general, if you've taken out your package in the last 24 hours, you may be able to change your itinerary for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a fee.

## 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.

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## Go further with the Expedia app

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![QR code to download the app](data:image/png;base64,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)