Title: Winchester Vacation Packages & Trips 2026 from CA $1,202 | 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. ![Best Western Chilworth Manor Hotel](https://images.trvl-media.com/lodging/1000000/860000/852900/852864/88ccb8b4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Best Western Chilworth Manor Hotel CA $1,202 per person Apr 8 - Apr 13 found 20 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Southampton (SOU) 8/10 Very Good! (1,002 reviews) Staff were really helpful and polite especially as it was twixtmas. The breakfast was really great. The rooms were clean, well maintained and spacious. Reviewed on Jan 3, 2026 ![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 $2,125 per person Feb 28 - Mar 5 found 1 day ago Roundtrip flight included Montreal (YUL) to Southampton (SOU) 9.6/10 Exceptional! (131 reviews) Lovely small hotel. Staff very friendly and efficient. Great cooked breakfast. Reviewed on Jan 3, 2026 ![room2 Southampton Hometel](https://images.trvl-media.com/lodging/23000000/22610000/22608700/22608660/884f1de7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### room2 Southampton Hometel Southampton City Centre CA $1,240 per person Apr 8 - Apr 13 found 20 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Southampton (SOU) 9.4/10 Exceptional! (1,156 reviews) Staff were very helpful. Room is very well maintained and it's a warm feeling through out. Reviewed on Jan 6, 2026 ![The Clarence Boutique Rooms](https://images.trvl-media.com/lodging/4000000/3250000/3246100/3246085/d0b1c7f5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Clarence Boutique Rooms Southsea CA $1,315 per person Apr 8 - Apr 13 found 20 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Southampton (SOU) 9.4/10 Exceptional! (248 reviews) Gorgeous hotel with lovely, polite & enthusiastic staff! We were upgraded to a fabulous suite & the parking options were great. We loved this unique boutique hotel which has been decorated & designed with care & passion. Local transport was brilliant & Southsea is a hidden blossoming gem which we’ll be back to see next year! We will of course be checking back in to the Clarence or one of its sisters. Thank you for making our stay so memorable x Reviewed on Sep 25, 2025 ![Village Hotel Basingstoke](https://images.trvl-media.com/lodging/42000000/41540000/41539700/41539699/1016f406_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Village Hotel Basingstoke CA $1,388 per person Mar 15 - Mar 20 found 4 hours ago Roundtrip flight included Toronto (YYZ) to Southampton (SOU) 8.8/10 Excellent! (765 reviews) Staff very attentive. Food was lovely. Great size bed, however the space in the room is limited. Reviewed on Jan 25, 2026 ### Things to do in and around Winchester Winchester offers a delightful blend of outdoor adventures and scenic beauty, making it perfect for a vacation. Key activities include exploring the recreational areas and vibrant public markets, as well as the famous Winchester Christmas Market. Don't miss out on the various shore excursions and unique trips that showcase the charm of this historic city. Whether you're seeking relaxation or adventure, Winchester has something for every traveller. **Shopping** In Winchester, enjoy local shops and boutiques for unique gifts. If you're up for a drive, visit WestQuay Shopping Centre, 19.3km away, for a vibrant shopping experience. Gunwharf Quays, 32.2km away, also offers a mix of outlets and entertainment, perfect for a day trip. **Recreation** The [Winchester Science Centre and Planetarium](https://www.expedia.ca/Winchester-Science-Centre-And-Planetarium-Winchester.d6265020.Vacation-Attraction) offers an engaging blend of education and fun, perfect for families. Enjoy cultural performances at the [Mayflower Theatre](https://www.expedia.ca/Mayflower-Theatre-The-Polygon.d6167566.Vacation-Attraction), ideal for a romantic night out. For a movie experience, [Leisure World](https://www.expedia.ca/Leisure-World-Southampton-City-Centre.d6224316.Vacation-Attraction) provides a relaxed atmosphere for entertainment with loved ones. **Adventure** Experience the thrill of speed at TeamSport Indoor Go Karting Southampton, located 9.7km from Winchester, where you can race against friends on an exciting track. Alternatively, visit Monkey Bizness, 11.3km away, for family-friendly arcade fun and adventure vibes. The Race Centre offers another exciting karting experience, also 9.7km from Winchester. **Nightlife** In Winchester, enjoy a lively nightlife at venues like The Old Gaolhouse and The Rifleman, where you can find cozy pubs and vibrant bars. Stroll along High Street for unique spots and live music, creating a warm atmosphere perfect for a memorable night out. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in and around Winchester Winchester offers a delightful blend of outdoor adventures and rich history, making it perfect for your vacation. Explore historic sites such as Winchester Cathedral, visit engaging museums, and discover charming historic houses. With attractions catering to culture and family experiences, you'll find plenty to keep you entertained. Don't miss the chance to immerse yourself in the captivating scenery and vibrant heritage of this remarkable city. - **[Winchester Cathedral: ](https://www.expedia.ca/Winchester-Cathedral-Winchester.d6092087.Vacation-Attraction)** Experience the grandeur of Winchester Cathedral, a stunning medieval structure with remarkable architecture and rich history. Explore its beautiful stained glass windows and tranquil atmosphere, making it a perfect spot for reflection and cultural appreciation. - **[Paultons Family Theme Park - Home of Peppa Pig World: ](https://www.expedia.ca/Paultons-Family-Theme-Park-Home-Of-Peppa-Pig-World-Romsey.d553248621562854464.Vacation-Attraction)** A delightful theme park located 20.9km from Winchester, perfect for families. Enjoy thrilling rides and attractions themed around the beloved characters from Peppa Pig, ensuring a fun-filled day for visitors of all ages. - **[University of Southampton: ](https://www.expedia.ca/University-Of-Southampton-Portswood.d6092063.Vacation-Attraction)** Situated 14.5km from Winchester, this historic university boasts impressive architecture and beautiful grounds. Explore its vibrant campus and engage with the culture of an esteemed institution known for its research and innovation. ### Best time to go to Winchester The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly cloudy with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 40.3°F (4.6°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 41.2°F (5.1°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | March | 43.9°F (6.6°C) | Light Rain | Mostly Cloudy | Average | Average | | April | 47.8°F (8.8°C) | Light Rain | Mostly Cloudy | Average | Average | | May | 53.2°F (11.8°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | | June | 59.2°F (15.1°C) | Light Rain | Mostly Cloudy | Average | Average | | July | 62.8°F (17.1°C) | Light Rain | Mostly Cloudy | Slightly High | Slightly High | | August | 62.1°F (16.7°C) | Light Rain | Mostly Cloudy | Average | Slightly High | | September | 58.6°F (14.8°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | October | 53.4°F (11.9°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | | November | 46.8°F (8.2°C) | Light Rain | Mostly Cloudy | Slightly High | Slightly Low | | December | 43.0°F (6.1°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | ### Tips to save on your trip to Winchester - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Winchester. - Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to Winchester. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## 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! (1,003 reviews) All staff very friendly & helpful. Had a great overnight stay Reviewed on Jan 24, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true®ionId=5477) [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true®ionId=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 7.8/10 Good! (1,001 reviews) Spotless rooms, lovely amenities, great location, fantastic staff. Reviewed on Dec 26, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=2773823&PinnedHotelID=2773823&HadPinnedHotel=true®ionId=5477) [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=2773823&PinnedHotelID=2773823&HadPinnedHotel=true®ionId=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 29 - Jan 30 includes taxes & fees 7.4/10 Good! (1,003 reviews) Great staff on reception. Very convenient location. Room was clean and well equipped. Reviewed on Jan 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F01%2F2026&endDate=30%2F01%2F2026&selected=4799&PinnedHotelID=4799&HadPinnedHotel=true®ionId=5477) [See all 3,127 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F01%2F2026&endDate=27%2F01%2F2026®ionId=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://images.trvl-media.com/place/6092087/ff73f055-5c52-4237-a7f2-d954af36dc4a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Winchester Cathedral 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://images.trvl-media.com/place/6265020/6552a2cd-b281-4265-abce-9f9d6c292463.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://images.trvl-media.com/place/6279761/d466cf36-50c2-47ca-869b-a8970c62a77a.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 $49 per adult [](https://expedia.ca/things-to-do/private-winchester-walking-tour.a48218822.activity-details) ![Southampton: Guided Ghost Walk](https://mediaim.expedia.com/localexpert/48074726/6d9a251e-6cbd-4a93-a4b1-b194887e4d43.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### The Southampton Ghost Walk CA $28 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/the-southampton-ghost-walk.a48074726.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 $43 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/private-southampton-walking-tour.a48105645.activity-details) [See all activities in Winchester](https://expedia.ca/things-to-do/search?rid=5477) ## Explore a world of travel with Expedia - 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[Bursledon Brickworks Industrial Museum ](https://www.expedia.ca/Bursledon-Brickworks-Industrial-Museum-Southampton.d6266327.Vacation-Attraction) - [Calshot Beach ](https://www.expedia.ca/Calshot-Beach-Southampton.d553248621532491462.Vacation-Attraction) - [City Museum ](https://www.expedia.ca/City-Museum-Winchester.d6092091.Vacation-Attraction) - [Visit Chandler's Ford ](https://www.expedia.ca/Eastleigh-Chandlers-Ford.dx553248634839114381) - [Fort Brockhurst ](https://www.expedia.ca/Fort-Brockhurst-Gosport.d6279818.Vacation-Attraction) - [Grosvenor Casino ](https://www.expedia.ca/Grosvenor-Casino-Southampton-City-Centre.d553248621532491127.Vacation-Attraction) - [Hms Victory ](https://www.expedia.ca/HMS-Victory-Portsmouth.d6092027.Vacation-Attraction) - [Highclere Castle ](https://www.expedia.ca/Highclere-Castle-Newbury.d6083943.Vacation-Attraction) - [Visit Hinton Ampner ](https://www.expedia.ca/Hinton-Ampner.dx3000402454) - [Hospital of St Cross ](https://www.expedia.ca/Hospital-Of-St-Cross-Winchester.d6279761.Vacation-Attraction) - 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[Riverside Park ](https://www.expedia.ca/Riverside-Park-Southampton.d6265277.Vacation-Attraction) - [Seacity Museum ](https://www.expedia.ca/SeaCity-Museum-Southampton-City-Centre.d6265167.Vacation-Attraction) - [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) \* Savings based on package bookings compared to the price of the same components booked separately. 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