Title: Winchester Vacation Packages & Trips 2026 from CA $1,104 | 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.

![Bournemouth West Cliff Hotel & Spa](https://images.trvl-media.com/lodging/1000000/20000/19700/19693/68ed4575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bournemouth West Cliff Hotel & Spa

Bournemouth City Centre

CA $1,104

per person

Feb 17 - Feb 20

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

7.8/10 Good! (1,002 reviews)

Lovely staff and well run hotel. Great value. A few shelves will help in the shower and a hand towel holder by the sink. Pool was great, spa disappointing (steam room out of order). Simple and fresh breakfast. Lovely waiting staff

Reviewed on Dec 31, 2025

![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 $1,247

per person

Mar 19 - Mar 25

found 5 hours ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

7.4/10 Good! (1,002 reviews)

Lovely view, nice staff. Great central location. Room was a bit tired, but spotlessly clean It was, sadly, very cold. Even with the heater on full blast it was chilly. I would certainly stay here again

Reviewed on Jan 8, 2026

![OYO The Lodge Bournemouth](https://images.trvl-media.com/lodging/91000000/90020000/90018900/90018804/ceb1c102_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### OYO The Lodge Bournemouth

Bournemouth City Centre

CA $1,195

per person

Feb 17 - Feb 20

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

8/10 Very Good! (12 reviews)

Lovely clean and comfortable room. Staff very friendly and welcoming. Perfectly located and fit for purpose.

Reviewed on Sep 7, 2024

![Langtry Manor Hotel](https://images.trvl-media.com/lodging/1000000/900000/893400/893390/26a6a399_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Langtry Manor Hotel

CA $1,223

per person

Feb 17 - Feb 20

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

8.6/10 Excellent! (369 reviews)

Tea, coffee available in the room

Reviewed on Dec 23, 2025

![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 $1,214

per person

Feb 16 - Feb 21

found 17 hours ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

8/10 Very Good! (575 reviews)

We stayed over night as we had a work party there. Room very comfortable. Nice friendly welcome when we checked in. The bar staff very very attentive and efficient. Food was lovey. Thank you

Reviewed on Dec 6, 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! (1,002 reviews)

Overall an great stay on problems experienced was we were given an out of order room at 1st by mistake as work was being done in the bathroom

Reviewed on Jan 2, 2026

[Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%2F01%2F2026&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true&regionId=5477)

[](https://expedia.ca/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%2F01%2F2026&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true&regionId=5477)

![Winchester Wessex Hotel by Sunday](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/3ac6caac_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Winchester Wessex Hotel by Sunday

Paternoster Row Winchester England

Fully refundableReserve now, pay when you stay

CA $97

CA $116 total

Jan 18 - Jan 19

includes taxes & fees

7.4/10 Good! (1,000 reviews)

Lovely view, nice staff. Great central location. Room was a bit tired, but spotlessly clean It was, sadly, very cold. Even with the heater on full blast it was chilly. I would certainly stay here again

Reviewed on Jan 8, 2026

[](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=4799&PinnedHotelID=4799&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 $351

CA $422 total

Jan 10 - Jan 11

includes taxes & fees

7.8/10 Good! (1,000 reviews)

Spotless rooms, lovely amenities, great location, fantastic staff.

Reviewed on Dec 26, 2025

[](https://expedia.ca/Hotel-Search?startDate=10%2F01%2F2026&endDate=11%2F01%2F2026&selected=2773823&PinnedHotelID=2773823&HadPinnedHotel=true&regionId=5477)

[See all 3,191 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F01%2F2026&endDate=10%2F01%2F2026&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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- [Sir Harold Hillier Gardens ](https://www.expedia.ca/Sir-Harold-Hillier-Gardens-Romsey.d6280602.Vacation-Attraction)
- [Solent Sky Museum ](https://www.expedia.ca/Solent-Sky-Museum-Southampton-City-Centre.d6169965.Vacation-Attraction)
- [Southampton City Art Gallery ](https://www.expedia.ca/Southampton-City-Art-Gallery-Southampton-City-Centre.d6259963.Vacation-Attraction)
- [Southampton Cruise Terminal ](https://www.expedia.ca/Southampton-Cruise-Terminal-Freemantle.d6156577.Vacation-Attraction)
- [Southampton Maritime Museum ](https://www.expedia.ca/Southampton-Maritime-Museum-Southampton-City-Centre.d6092057.Vacation-Attraction)
- [Southampton Vacations ](https://www.expedia.ca/Southampton.d3245.Destination-Travel-Guides)
- [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)

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