--- title: "Winsor Vacation Packages & Trips 2026 from CA $1,505 | Expedia" description: "FREE cancellation on select hotels Bundle Winsor flight and hotel to build your own Winsor vacation package & you can 𝘀𝗮𝘃𝗲 with Expedia! Choose from thousands of Winsor holiday trips & travel deals." canonical: "https://www.expedia.ca/Winsor.d3000381484.Destination-Travel-Guides" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-13T21:22:31Z --- ![A forested area with a dirt path, tall trees, and dense underbrush.](https://images.trvl-media.com/place/3000381484/8babd6a8-30e6-4da0-97ec-a8c79df3f3e3.jpg?impolicy=fcrop&w=1200&h=300&q=medium) Photo by Jim Champion # Winsor Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $4,200 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. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A transparent dome structure with a table and chairs inside, surrounded by a garden with string lights and a pond.](https://images.trvl-media.com/lodging/2000000/1390000/1382500/1382464/8b31672c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A traditional brick building with multiple gabled roofs, a paved driveway, and a stone pillar with a lamp post.](https://images.trvl-media.com/lodging/2000000/1390000/1382500/1382464/b02169a0.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Dec 25 - Dec 29** ### [The Casa Hotel, Sure Hotel Collection by Best Western + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-25/2026-12-29/?FromAirport=YYZ&Destination=SOU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1382464&dealMarker=&paandie=true&cabinClass=e) Yateley 3 nights **8.2/10** \- Very good (533 reviews) "The property was advertised as being pet-friendly but on arrival they couldn’t accommodate our King Charles Cavalier so I had to travel home to Kent with my dog, leaving my daughter and partner at the hotel. I then had to travel back to the hotel early the next morning to collect my family." Reviewed October 31, 2026 Roundtrip • Toronto (YYZ) - Southampton (SOU) YYZ - LHR • 2 stops LHR - YYZ • 2 stops [~~CA $1,571~~](https://www.expedia.ca/) **CA $1,505** per traveller found 1 day ago ## Winsor Hotel Deals ### [Woodlands Hotel](https://www.expedia.ca/Southampton-Hotels-Woodlands-Lodge-Hotel.h2163195.Hotel-Information) ![A large house with a well-maintained lawn and trees in the foreground.](https://images.trvl-media.com/lodging/3000000/2170000/2163200/2163195/70166a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Bartley Road, Southampton, England, SO40 7GN, GB - Location: 2.9 km from Winsor - Star rating: 3/5 - Guest rating: 8.6/10 (Excellent, 405 reviews) - Price: CA $89, CA $107 total, includes taxes & fees, Nov 15 - Nov 16 ### [The Crown Manor House Hotel](https://www.expedia.ca/Lyndhurst-Hotels-The-Crown-Manor-House-Hotel.h22746.Hotel-Information) ![A grand staircase with a large elk sculpture, a chandelier, and a cozy seating area with a fireplace.](https://images.trvl-media.com/lodging/1000000/30000/22800/22746/6091e4fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: High Street, Lyndhurst, England, SO43 7NF, GB - Location: 6.3 km from Winsor - Star rating: 4/5 - Guest rating: 9.2/10 (Wonderful, 1001 reviews) - Price: CA $140, CA $168 total, includes taxes & fees, Nov 15 - Nov 16 ### [The Mortimer Arms](https://www.expedia.ca/Romsey-Hotels-The-Mortimer-Arms.h2279562.Hotel-Information) ![A cozy room with a fireplace, a round wooden table, and a bar area.](https://images.trvl-media.com/lodging/3000000/2280000/2279600/2279562/8efb82a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: The Mortimer Arms, Romsey Road, Ower, Romsey, England, SO51 6AF, GB - Location: 2.4 km from Winsor - Star rating: 4/5 - Guest rating: 8.6/10 (Excellent, 332 reviews) - Price: CA $127, CA $153 total, includes taxes & fees, Nov 15 - Nov 16 - Review: ………………………………………………………………. ### [The White Horse Hotel, Romsey, Hampshire](https://www.expedia.ca/Romsey-Hotels-The-White-Horse-Hotel-Romsey.h2597.Hotel-Information) ![A traditional room with a fireplace, multiple seating areas, and a large window.](https://images.trvl-media.com/lodging/1000000/10000/2600/2597/1492aaca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Market Place, Romsey, England, SO51 8ZJ, GB - Location: 7.8 km from Winsor - Star rating: 4/5 - Guest rating: 9.2/10 (Wonderful, 749 reviews) - Price: CA $109, CA $130 total, includes taxes & fees, Nov 15 - Nov 16 ### [The New Forest Inn](https://www.expedia.ca/Lyndhurst-Hotels-The-New-Forest-Inn.h36186655.Hotel-Information) ![A row of traditional Tudor-style buildings with brick chimneys and white timber framing.](https://images.trvl-media.com/lodging/37000000/36190000/36186700/36186655/0f7471fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: The New Forest Inn, Emery Down, Lyndhurst, England, SO43 7DY, GB - Location: 6.6 km from Winsor - Star rating: 2.5/5 - Guest rating: 9.4/10 (Exceptional, 195 reviews) - Price: CA $140, CA $168 total, includes taxes & fees, Nov 17 - Nov 18 - Review: The hotel was further from Lyndhurst than I expected and although that wasn't an issue, it was further than I anticipated. This for us was the only downside to the stay. The room was cosy and comfortable and somewhat quirky. We loved its uniqueness. The hotel restaurant was lovely and we enjoyed our dinner there on our overnight stay. We would definitely stay again as it was convenient for a stop over before embarking on a cruise the following day from Southampton. ### [The Bell Inn](https://www.expedia.ca/Lyndhurst-Hotels-The-Bell-Inn.h9727604.Hotel-Information) ![A cozy room with a fireplace, a sofa, a dining table with a menu, and a bookshelf.](https://images.trvl-media.com/lodging/10000000/9730000/9727700/9727604/43dc6e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Brook, Lyndhurst, England, SO43 7HE, GB - Location: 4.4 km from Winsor - Star rating: 4/5 - Guest rating: 9/10 (Wonderful, 137 reviews) - Price: CA $176, CA $211 total, includes taxes & fees, Nov 15 - Nov 16 - Review: Nice hotel in a great location. We enjoyed our stay ### [The Pilgrim Inn](https://www.expedia.ca/Southampton-Hotels-The-Pilgrim-Inn.h4053099.Hotel-Information) ![A cozy restaurant with wooden furniture, brick walls, and framed artwork.](https://images.trvl-media.com/lodging/5000000/4060000/4053100/4053099/fe654ee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Hythe Road, Southampton, England, SO40 4WU, GB - Location: 8.5 km from Winsor - Star rating: 4.5/5 - Guest rating: 9.2/10 (Wonderful, 861 reviews) - Price: CA $156, CA $187 total, includes taxes & fees, Nov 15 - Nov 16 - Review: Staff are very friendly ### [The Duke on The Test](https://www.expedia.ca/Romsey-Hotels-The-Duke-On-The-Test.h83209137.Hotel-Information) ![A cozy restaurant with a bar area, wooden tables, and a mural on the wall.](https://images.trvl-media.com/lodging/84000000/83210000/83209200/83209137/35326d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: Greatbridge Rd, Romsey, England, SO51 0HB, GB - Location: 9.6 km from Winsor - Star rating: 5/5 - Guest rating: 9.4/10 (Exceptional, 160 reviews) - Price: CA $116, CA $139 total, includes taxes & fees, Nov 15 - Nov 16 - Review: Short stay but very nice hotel, spacious rooms and great breakfast. 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. [See all properties in Winsor](https://www.expedia.ca/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28®ionId=3000381484&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Frequently Asked Questions ### How much does a Winsor vacation package cost? You'll find cheap prices from CA $1,505 on Expedia for your Winsor break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Winsor costs. ### What are the cheapest months to go to Winsor? You can generally find lower prices and better availability in January, February and November. Browse our cheap Winsor vacation packages and you could get some great off-season deals. ### How many days is enough for Winsor? We recommend booking a Winsor vacation for at least 2 days. This will allow you enough time to check off popular sights including [Romsey Golf Club](https://www.expedia.ca/Romsey-Golf-Club-Southampton.d6261192.Vacation-Attraction) and [Delta Force Paintball Southampton](https://www.expedia.ca/Delta-Force-Paintball-Southampton-Southampton.d553248621532491132.Vacation-Attraction), and also check out neighbourhoods like Shirley and Nursling. You could even make time for a day trip from Winsor. ### How to find the best Winsor package deals? Start your search for a Winsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winsor package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winsor adventure off to a flying start. ### Is it cheaper to book a Winsor vacation as a package? An Expedia vacation package could score you significant savings when compared to arranging flights and stays separately. Better still, you can tailor your Winsor escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save. ### When to book a vacation package to Winsor? Enjoy fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Winsor trip. ### How to plan a trip to Winsor? 1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Winsor. 2. Set your budget: Factor in costs like flights, food and transportation when working out how much to put aside for your trip to Winsor. Then, choose a hotel that matches your budget, whether that's an economical option or a deluxe getaway. 3. Decide how long to go away for: Now that you're up to speed on Winsor, you can figure out the perfect length of your vacation. Pull together a rough itinerary and give yourself enough time to get through everything on your must-do list. 4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Winsor vacation package. ## Explore a world of travel with Expedia - [Lodging](?equalTargetTab=tab-0) - [Flights](?equalTargetTab=tab-1) - [Packages](?equalTargetTab=tab-2) - [Cars](?equalTargetTab=tab-3) - [Vacation Rentals](?equalTargetTab=tab-4) - [Things to do](?equalTargetTab=tab-5) - [Cottages in Southampton](https://www.expedia.ca/Southampton-Cottages.d3245-aaCottages.Travel-Guide-Accommodation) - [Lgbt Friendly Hotels in Romsey](https://www.expedia.ca/Romsey-Hotels-LGBT-Friendly-Hotel.0-0-d5671-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Capsule Hotels in Southampton](https://www.expedia.ca/Southampton-Capsule-Hotels.d3245-aaCapsuleHotels.Travel-Guide-Accommodation) - [Hotels with Hot Tubs in Southampton](https://www.expedia.ca/Southampton-Hotels-Hotels-With-Hot-Tubs.0-0-d3245-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Southampton City Centre Hotels](https://www.expedia.ca/Southampton-City-Centre-Southampton-Hotels.0-n553248635810423085-0.Travel-Guide-Filter-Hotels) - 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[National Car Rental Rental Cars in Southampton](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Southampton.d3245-c42.Car-Rental-Guide-Suppliers) - [Car rentals near Southampton Cruise Terminal](https://www.expedia.ca/Car-Rentals-In-Southampton-Cruise-Terminal.d6156577.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in Southampton](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-Southampton.d3245-c43.Car-Rental-Guide-Suppliers) - [Car rentals near New Forest District](https://www.expedia.ca/Destinations-In-New-Forest-District.d553248635976007408.Car-Rental-Destinations) - [Avis Rental Cars in Southampton](https://www.expedia.ca/Avis-Car-Rentals-In-Southampton.d3245-c41.Car-Rental-Guide-Suppliers) - [Car rental Southampton](https://www.expedia.ca/Car-Rentals-In-Southampton.d3245.Car-Rental-Guide) - [Southampton Vacation Rentals](https://www.expedia.ca/Southampton-Vacation-Rentals.d3245.Travel-Guide-VacationRentals) - [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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