Title: Winchester Vacation Packages & Trips 2026 from CA $1,005 | Expedia.ca

[Winchester Travel Guide](https://expedia.ca/Winchester.dx5477)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d5477.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d5477.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d5477.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d5477.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d5477.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248621533024470/bf655068-0bc4-49d6-8aa5-906a3dc0fc77.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# 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 Winchester Vacation

The rich history and welcoming locals are just the start of the things Winchester has on offer. Discover the very best of this city the way you want with a customized Winchester vacation package. If your trip to Winchester includes a little sightseeing, visit popular attractions like [Winchester Cathedral](https://www.expedia.ca/Winchester-Cathedral-Winchester.d6092087.Vacation-Attraction), [Great Hall](https://www.expedia.ca/Great-Hall-Winchester.d6092089.Vacation-Attraction) and [Winchester Christmas Market](https://www.expedia.ca/Winchester-Christmas-Market-Winchester.d553248621563222633.Vacation-Attraction). Whoever you're escaping with and whatever the size of your budget, your ultimate Winchester vacation is only clicks away with Expedia.

## Top Winchester Vacation Deals

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

![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 $1,005

per person

Jan 21 - Jan 25

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

7.4/10 Good! (1,002 reviews)

Great bed and fantastic view of cathedral. Unfortunately room and bathroom felt very stale and dated. Would prefer better parking options. Very noisy air con. Also shocked at £5 charge to leave bags temporarily at end of stay.

Reviewed on Dec 7, 2025

![Warbrook House Heritage Hotel](https://images.trvl-media.com/lodging/2000000/1660000/1652700/1652697/35e41764_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Warbrook House Heritage Hotel

CA $1,085

per person

Feb 17 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Southampton (SOU)

7.6/10 Good! (796 reviews)

Lovely check in by the young irish lady! Very welcoming- had tea while waiting, possibly the dirtiest milk jug i have ever seen. The whole hotel is old and dated, with a bit of painting and new carpet and some interior design could have a lot more charm- comfy clean room (curtains missing multiple rings so hung all lopsided), had a shower- towels we’re in the wardrobe in the other room 😎 just odd things- it’s on the cusp of being charming but misses it… not a 4 star place as advertised, but nice non the less.

Reviewed on Dec 1, 2025

![Alton House Hotel](https://images.trvl-media.com/lodging/2000000/1930000/1929200/1929179/e7ff482e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Alton House Hotel

CA $1,068

per person

Feb 17 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Southampton (SOU)

8/10 Very Good! (570 reviews)

Excellent Staff. Very Welcoming. Room Dated but spotless. Lots of parking. Only thing not giving 5 Stars is the Commmon areas and Bathroom very dated. Carpets very worn in places. Some refurbishment underway . Location Excellent. No hesitation in recommending.

Reviewed on Dec 5, 2025

## Ready to book your vacation to Winchester?

Choose your dates

## 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

8.4/10 Very Good! (1,000 reviews)

Very helpful and polite Reception team and Spa Team .. Spa was excellent.. pleasant Hotel entrance…

Reviewed on Dec 9, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=25%2F12%2F2025&endDate=26%2F12%2F2025&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true&regionId=5477)

[](https://expedia.ca/Hotel-Search?startDate=25%2F12%2F2025&endDate=26%2F12%2F2025&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true&regionId=5477)

![voco Winchester Hotel & Spa by IHG](https://images.trvl-media.com/lodging/4000000/3440000/3430900/3430824/bec3fe8c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

voco Winchester Hotel & Spa by IHG

Telegraph Way Morn Hill Winchester England

Fully refundable

CA $128

CA $190 total

Dec 26 - Dec 27

includes taxes & fees

8.6/10 Excellent! (927 reviews)

Stayed for one night to attend an event in central Winchester, which is a 10 minute drive away. The room itself was lovely and clean. The breakfast was excellent - lots of variety for all appetites and tastes. Was replenished regularly. Wouldn’t hesitate to stay again!

Reviewed on Dec 6, 2025

[](https://expedia.ca/Hotel-Search?startDate=26%2F12%2F2025&endDate=27%2F12%2F2025&selected=3430824&PinnedHotelID=3430824&HadPinnedHotel=true&regionId=5477)

![Norton Park Hotel, Spa & Manor House](https://images.trvl-media.com/lodging/3000000/2780000/2773900/2773823/757d6db6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Norton Park Hotel, Spa & Manor House

Sutton Scotney Winchester England

Fully refundableReserve now, pay when you stay

CA $131

CA $157 total

Jan 5 - Jan 6, 2026

includes taxes & fees

7.8/10 Good! (1,004 reviews)

Excellent stay in wonderful grounds.Brilliant staff and great food choices.Room comfortable and clean.

Reviewed on Dec 5, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=2773823&PinnedHotelID=2773823&HadPinnedHotel=true&regionId=5477)

[See all 3,198 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F12%2F2025&endDate=13%2F12%2F2025&regionId=5477)

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)

### Discover the most popular places to visit in Winchester

![Winchester Cathedral featuring a park, heritage architecture and a church or cathedral](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/127000/127174-Winchester-Cathedral.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Winchester Cathedral

5/5(17 reviews)

With its exquisite artwork and fascinating historical relics, Winchester’s Gothic masterpiece is thought to be one of the nation’s finest cathedrals.

[](https://expedia.ca/Winchester-Cathedral-Winchester.d6092087.Vacation-Attraction)

![Winchester Science Centre and Planetarium](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/126000/126835-Winchester.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Winchester Science Centre and Planetarium

Try out an extensive selection of interactive exhibits and lose yourself in deep space at one of the U.K.’s largest digital planetariums.

[](https://expedia.ca/Winchester-Science-Centre-And-Planetarium-Winchester.d6265020.Vacation-Attraction)

![Hospital of St Cross featuring heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/127000/127488-Hospital-Of-St-Cross.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Hospital of St Cross

Set within tranquil gardens, England’s oldest charitable institution features traditional 15th-century architecture and a stunning Norman church.

[](https://expedia.ca/Hospital-Of-St-Cross-Winchester.d6279761.Vacation-Attraction)

### What to do in Winchester

![Private Winchester Walking Tour](https://mediaim.expedia.com/localexpert/48218822/3507caed-57ca-48c0-bb27-a52bb3ea7c44.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Private Winchester Walking Tour

CA $48

per adult

[](https://expedia.ca/things-to-do/private-winchester-walking-tour.a48218822.activity-details)

![Private Southampton Walking Tour](https://mediaim.expedia.com/localexpert/48105645/1120b595-6fa1-42e9-b69a-e4a6b05f47ad.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Private Southampton Walking Tour

CA $42

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/private-southampton-walking-tour.a48105645.activity-details)

![Winchester: Guided Alfred the Great Haunted Ghost Tour](https://mediaim.expedia.com/localexpert/49391309/27aef1fd-f11e-4c10-8c82-9847d205d914.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Winchester: King Alfred the Great Haunted Ghost Tour

CA $22

per adult

[](https://expedia.ca/things-to-do/winchester-king-alfred-the-great-haunted-ghost-tour.a49391309.activity-details)

[See all activities in Winchester](https://expedia.ca/things-to-do/search?rid=5477)

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- [Tudor House and Garden ](https://www.expedia.ca/Tudor-House-And-Garden-Southampton-City-Centre.d6261206.Vacation-Attraction)
- [Winchester Cathedral ](https://www.expedia.ca/Winchester-Cathedral-Winchester.d6092087.Vacation-Attraction)
- [Winchester City Mill ](https://www.expedia.ca/Winchester-City-Mill-Winchester.d6258721.Vacation-Attraction)
- [Winchester Science Centre and Planetarium ](https://www.expedia.ca/Winchester-Science-Centre-And-Planetarium-Winchester.d6265020.Vacation-Attraction)
- [Winsor Vacations ](https://www.expedia.ca/Winsor.d3000381484.Destination-Travel-Guides)

- [Car rental Eastleigh ](https://www.expedia.ca/Car-Rentals-In-Eastleigh.d4631.Car-Rental-Guide)
- [Car rentals near The Race Centre ](https://www.expedia.ca/Car-Rentals-In-The-Race-Centre.d553248621532491559.Car-Rental-Guide)
- [Car rentals near Hampshire ](https://www.expedia.ca/Destinations-In-Hampshire.d603237.Car-Rental-Destinations)

- [Hampshire Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hampshire.d603237.Vacation-Rental-Destinations)

\* 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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