Title: Winsor Vacation Packages & Trips 2026 from CA $1,279 | Expedia.ca [Winsor Travel Guide](https://expedia.ca/Winsor.dx3000381484)[Hotels in Winsor](https://expedia.ca/Winsor-Hotels.d3000381484.Travel-Guide-Hotels)[Vacation Rentals in Winsor](https://expedia.ca/Winsor-Vacation-Rentals.d3000381484.Travel-Guide-VacationRentals)[Winsor Car Rentals](https://expedia.ca/Car-Rentals-In-Winsor.d3000381484.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winsor 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 Winsor Vacation Reserve a Winsor vacation package that has everything you need without any unnecessary extras. Great for dining, cafes and bars and pubs, consider basing yourself in the neighborhood of Southampton City Centre. You'll want to go sightseeing during your trip to Winsor. Find time for major attractions such as [New Forest Wildlife Park](https://www.expedia.ca/New-Forest-Wildlife-Park-Southampton.d6265169.Vacation-Attraction), [The Common](https://www.expedia.ca/The-Common-Southampton.d553248621532491129.Vacation-Attraction) and [Romsey Golf Club](https://www.expedia.ca/Romsey-Golf-Club-Southampton.d6261192.Vacation-Attraction). Stop dreaming and start traveling. Explore the multitude of options on Expedia today and put your Winsor vacation plans in motion! ## Top Winsor Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Winchester Wessex Hotel by Sunday](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/5efbbf93_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winchester Wessex Hotel by Sunday CA $1,279 per person Apr 21 - Apr 27 found 8 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Southampton (SOU) 7.6/10 Good! (1,002 reviews) Clean room, good and friendly staff. Reviewed on Mar 1, 2026 ![Shepherd's Hut in Romsey With Fire Pit](https://images.trvl-media.com/lodging/117000000/116080000/116074000/116073982/5233c1e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Shepherd's Hut in Romsey With Fire Pit CA $2,257 per person May 21 - May 25 found 8 hours ago Roundtrip non-stop flight included Montreal (YUL) to Southampton (SOU) No reviews ![Sandy Balls Holiday Village](https://images.trvl-media.com/lodging/83000000/82960000/82956600/82956532/5a2a3c11_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sandy Balls Holiday Village CA $1,951 per person May 21 - May 25 found 8 hours ago Roundtrip non-stop flight included Montreal (YUL) to Southampton (SOU) 8.4/10 Very Good! (105 reviews) Not our first stay at this park and as is the norm in our experience staff were polite and helpful, the accomadation was clean and funtional. We ate at the tavern and the food was of good quality and plentiful, also affordable and in line with other local eateries. We love the convenience of this park and will stay again in the coming future. Highly recommend to anyone who has not yet found this little gem! Reviewed on Nov 8, 2025 ![The Star and Garter](https://images.trvl-media.com/lodging/16000000/15640000/15636100/15636067/db6a81e4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Star and Garter CA $1,725 per person May 21 - May 25 found 8 hours ago Roundtrip non-stop flight included Montreal (YUL) to Southampton (SOU) 8.8/10 Excellent! (405 reviews) I chose this hotel due to its location, being right in the centre of the town, so we could walk to restaurants and pubs in the evenings, with the cost being reasonable. The breakfast was a bit expensive, but there are various cafes only a short walk away which are cheaper, so you could go for the room only option. Ask for a room at the back, as the front rooms are facing onto the junction of the main pedestrianised area and through road, so it can get a bit noisier at night at the weekend. The rooms were functional and clean, but there was a lack of drawers for longer stays. The breakfast was good, with no restriction on how much you could have, and in a nice room, so it was a relaxed start to the day Reviewed on Sep 15, 2025 ![White Hart, Andover by Marston's Inns](https://images.trvl-media.com/lodging/33000000/32620000/32618000/32617953/d75b6dc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### White Hart, Andover by Marston's Inns CA $1,645 per person May 21 - May 25 found 8 hours ago Roundtrip non-stop flight included Montreal (YUL) to Southampton (SOU) 7.4/10 Good! (428 reviews) How to rate this place; well it was perfectly adequate in most ways, well below satisfactory for the discerning and as I overhead the Aussie backpackers saying a few table over at breakfast ‘bloody brilliant’. So it is what you’d expect. And how you rate it depends on what’s important to you and your level of relativity to the outside world. Cheap - and it was! Dated and shabby - in a typical old English pub kind of way. This had its own charm, like the labyrinth of corridors and tiny up and down stair cases to get to the rooms.but also downfalls, like mismatched pain colour in the room where obviously once a painting hung and a toilet roll holder hanging on by a loose screw. Clean (enough) but not really. Some would’ve thought it fine, I wasn’t letting my kids roll around and play on the carpet. Comfy beds. New mattress and crisp linen, although the making could’ve been improved. Great location. Central, in the heart of Andover and will enough parking. Would I recommend it for a weekend away to impress the missus? Nup. A quick stopover on the way through? Yep if you can put up with the foibles and just want a cheap sleep. Reviewed on Jan 2, 2026 ## Ready to book your vacation to Winsor? Choose your dates ## Winsor Hotel Deals ![Leonardo Hotel Southampton ](https://images.trvl-media.com/lodging/2000000/1180000/1178300/1178290/05076bde_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Leonardo Hotel Southampton 1 Charlotte Place Southampton England Fully refundableReserve now, pay when you stay CA $95 CA $114 total Mar 22 - Mar 23 includes taxes & fees 8.6/10 Excellent! (1,267 reviews) Great location at a reasonable price. Spend the extra £5 for the full breakfast. No AC if you are there in the summer Reviewed on Mar 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=1178290&PinnedHotelID=1178290&HadPinnedHotel=true®ionId=3000381484) ![Novotel Southampton](https://images.trvl-media.com/lodging/1000000/10000/4500/4431/91305532_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Novotel Southampton 1 West Quay Road Southampton England Fully refundableReserve now, pay when you stay CA $77 CA $92 total Apr 12 - Apr 13 includes taxes & fees 8.2/10 Very Good! (1,002 reviews) Food appalling Room cool to cold Reviewed on Mar 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=4431&PinnedHotelID=4431&HadPinnedHotel=true®ionId=3000381484) ![Moxy Southampton](https://images.trvl-media.com/lodging/43000000/42110000/42101700/42101688/832abf4d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Moxy Southampton Harbour Parade Southampton England Fully refundableReserve now, pay when you stay CA $88 CA $106 total Mar 20 - Mar 21 includes taxes & fees 9/10 Wonderful! (1,004 reviews) Great location Reviewed on Mar 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F03%2F2026&endDate=21%2F03%2F2026&selected=42101688&PinnedHotelID=42101688&HadPinnedHotel=true®ionId=3000381484) [See all 2,792 properties in Winsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F03%2F2026&endDate=18%2F03%2F2026®ionId=3000381484) 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 Winsor ![Southampton Cruise Terminal](https://images.trvl-media.com/place/6156577/06e47e05-6d9c-4858-a50d-bdbfdd026b0d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Southampton Cruise Terminal One of the busiest cruise ports in England is just a few steps from the historical and entertainment attractions of Southampton. [](https://expedia.ca/Southampton-Cruise-Terminal-Freemantle.d6156577.Vacation-Attraction) ![University of Southampton](https://images.trvl-media.com/place/6092063/7ac07444-c8d0-48d3-bdcd-99b8b9ea57b8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Southampton Tour an oceanographic research institute, watch independent theater productions and see designs by notable British architects at this 150-year-old university. [](https://expedia.ca/University-Of-Southampton-Portswood.d6092063.Vacation-Attraction) ![Mayflower Theatre which includes signage and theatre scenes](https://images.trvl-media.com/place/6167566/601d46f7-1f79-4d7f-900e-14b76c57f01d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Mayflower Theatre From touring West End musicals to magic shows, stand-up comedy to children’s entertainment, this historic theater serves up Southampton’s best entertainment. [](https://expedia.ca/Mayflower-Theatre-The-Polygon.d6167566.Vacation-Attraction) ### What to do in Winsor ![Isle of Wight: Osborne Admission Ticket](https://mediaim.expedia.com/localexpert/5213559/94be67f4-c3bb-4f96-a63b-77dd36973a4d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Isle of Wight: Osborne Admission Ticket CA $15 per traveller **100%** of travellers recommend [](https://expedia.ca/things-to-do/isle-of-wight-osborne-admission-ticket.a5213559.activity-details) ![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 $43 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/private-southampton-walking-tour.a48105645.activity-details) [See all activities in Winsor](https://expedia.ca/things-to-do/search?rid=3000381484) ## Explore a world of travel with Expedia - 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[Solent Sky Museum ](https://www.expedia.ca/Solent-Sky-Museum-Southampton-City-Centre.d6169965.Vacation-Attraction) - [Visit Bassett ](https://www.expedia.ca/Southampton-Bassett.dx913911269248122880) - [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) - [Visit Freemantle ](https://www.expedia.ca/Southampton-Freemantle.dx913898648283316224) - [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) - [Visit Southampton ](https://www.expedia.ca/Southampton.dx3245) - [Sway Vacations ](https://www.expedia.ca/Sway.d6084894.Destination-Travel-Guides) - [Visit Totton ](https://www.expedia.ca/Totton.dx6257748) - [Tudor House and Garden ](https://www.expedia.ca/Tudor-House-And-Garden-Southampton-City-Centre.d6261206.Vacation-Attraction) - 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[Car rentals near Southampton Cruise Terminal ](https://www.expedia.ca/Car-Rentals-In-Southampton-Cruise-Terminal.d6156577.Car-Rental-Guide) - [Car rental Woodlands ](https://www.expedia.ca/Car-Rentals-In-Woodlands.d6130578.Car-Rental-Guide) - [Car rentals near New Forest District ](https://www.expedia.ca/Destinations-In-New-Forest-District.d553248635976007408.Car-Rental-Destinations) - [Southampton Vacation Rentals ](https://www.expedia.ca/Southampton-Vacation-Rentals.d3245.Travel-Guide-VacationRentals) - [Things to do in Minstead ](https://www.expedia.ca/Things-To-Do-In-Minstead.d3000387455.Travel-Guide-Activities) - [Things to do in Romsey ](https://www.expedia.ca/Things-To-Do-In-Romsey.d5671.Travel-Guide-Activities) - [Things to do in Southampton ](https://www.expedia.ca/Things-To-Do-In-Southampton.d3245.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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