Title: Winsor Vacation Packages & Trips 2026 from CA $919 | 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.

![The Elephant at the Market](https://images.trvl-media.com/lodging/91000000/90500000/90491300/90491219/d6a733ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Elephant at the Market

CA $919

per person

Mar 21 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Southampton (SOU)

8.2/10 Very Good! (176 reviews)

Nice staff. Great central location with parking. The room was lovely and very comfortable.

Reviewed on Jan 7, 2026

![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 $1,237

per person

Apr 3 - Apr 9

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

7.4/10 Good! (1,002 reviews)

Great staff on reception. Very convenient location. Room was clean and well equipped.

Reviewed on Jan 18, 2026

![Holiday Inn Farnborough by IHG](https://images.trvl-media.com/lodging/1000000/10000/1700/1644/06b8a75e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Farnborough by IHG

Rushmoor District

CA $1,281

per person

Mar 12 - Mar 18

found 7 hours ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

8.4/10 Very Good! (616 reviews)

Friendly staff, clean and good breakfast

Reviewed on Dec 28, 2025

![Original White Hart, Ringwood by Marston's Inns](https://images.trvl-media.com/lodging/12000000/11910000/11900100/11900019/79e8aa2d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Original White Hart, Ringwood by Marston's Inns

CA $1,098

per person

Apr 6 - Apr 12

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Southampton (SOU)

7.4/10 Good! (248 reviews)

Room good value for money, lovely central location with on site parking. Staff incredibly polite and very helpful.

Reviewed on Dec 9, 2025

![Audleys Wood Hotel](https://images.trvl-media.com/lodging/1000000/30000/20300/20250/fdac819b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Audleys Wood Hotel

CA $3,075

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

9.2/10 Wonderful! (435 reviews)

Very professional and helpful staff throughout the hotel. Beautiful, large suites with added touches such as Christmas trees, and full amenities. Wonderful stay. We will return.

Reviewed on Jan 5, 2026

## Ready to book your vacation to Winsor?

Choose your dates

## Winsor Hotel Deals

![Novotel Southampton](https://images.trvl-media.com/lodging/1000000/10000/4500/4431/cebf2d75_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Novotel Southampton

1 West Quay Road Southampton England

Fully refundableReserve now, pay when you stay

CA $79

CA $95 total

Feb 15 - Feb 16

includes taxes & fees

8/10 Very Good! (1,002 reviews)

Yes

Reviewed on Jan 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=4431&PinnedHotelID=4431&HadPinnedHotel=true&regionId=3000381484)

![Leonardo Royal Southampton Grand Harbour](https://images.trvl-media.com/lodging/1000000/20000/20000/19955/662fccb6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Leonardo Royal Southampton Grand Harbour

West Quay Road Southampton England

Fully refundableReserve now, pay when you stay

CA $102

CA $123 total

Feb 15 - Feb 16

includes taxes & fees

8.6/10 Excellent! (1,730 reviews)

nice stay

Reviewed on Jan 27, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=19955&PinnedHotelID=19955&HadPinnedHotel=true&regionId=3000381484)

![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=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true&regionId=3000381484)

[](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=26080&PinnedHotelID=26080&HadPinnedHotel=true&regionId=3000381484)

[See all 2,721 properties in Winsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F01%2F2026&endDate=31%2F01%2F2026&regionId=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

![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 Winsor](https://expedia.ca/things-to-do/search?rid=3000381484)

## Explore a world of travel with Expedia

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- [Car rental Romsey ](https://www.expedia.ca/Car-Rentals-In-Romsey.d5671.Car-Rental-Guide)
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- [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. Savings not available on all packages.

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