Title: Winsor Vacation Packages & Trips 2026 from CA $1,062 | 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.

![Holiday Inn Basingstoke by IHG](https://images.trvl-media.com/lodging/1000000/10000/4200/4156/ab25de28_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Basingstoke by IHG

CA $1,062

per person

Apr 29 - May 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

8.2/10 Very Good! (567 reviews)

Clean room Good price Happy with the hotel

Reviewed on Dec 2, 2025

![Chalet for 2 Persons in Droxford](https://images.trvl-media.com/lodging/117000000/116130000/116121700/116121651/09a913a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chalet for 2 Persons in Droxford

CA $1,650

per person

Apr 30 - May 4

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Southampton (SOU)

No reviews

![No.4 Carlton Hotel](https://images.trvl-media.com/lodging/92000000/91410000/91400200/91400160/6b09c3fb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### No.4 Carlton Hotel

The Polygon

CA $1,827

per person

Apr 30 - May 4

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Southampton (SOU)

9.6/10 Exceptional! (137 reviews)

Lovely small hotel. Staff very friendly and efficient. Great cooked breakfast.

Reviewed on Jan 3, 2026

![Village Hotel Basingstoke](https://images.trvl-media.com/lodging/42000000/41540000/41539700/41539699/a56a6130_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Village Hotel Basingstoke

CA $1,087

per person

Apr 29 - May 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

8.8/10 Excellent! (827 reviews)

Cant complain about anything. 5 star

Reviewed on Feb 25, 2026

![Best Western Chilworth Manor Hotel](https://images.trvl-media.com/lodging/1000000/860000/852900/852864/2b6baefa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Best Western Chilworth Manor Hotel

CA $1,201

per person

Apr 30 - May 4

found 8 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Southampton (SOU)

8/10 Very Good! (1,001 reviews)

Bed was comfortable, room was spotlessly clean. However the general appearance was of a very tierd decorations, fixtures and fittings. Needs an upgrade.

Reviewed on Feb 27, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_3000381484)

## Ready to book your vacation to Winsor?

Choose your dates

## Winsor Hotel Deals

![Novotel Southampton](https://images.trvl-media.com/lodging/1000000/10000/4500/4431/91305532_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Novotel Southampton

1 West Quay Road Southampton England

Fully refundableReserve now, pay when you stay

CA $84

CA $100 total

Mar 8 - Mar 9

includes taxes & fees

8/10 Very Good! (1,006 reviews)

The staff are friendly and approachable

Reviewed on Feb 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=4431&PinnedHotelID=4431&HadPinnedHotel=true&regionId=3000381484)

![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 $96

CA $116 total

Mar 22 - Mar 23

includes taxes & fees

8.6/10 Excellent! (1,264 reviews)

Lovely clean room, friendly staff, overall a brilliant stay. The only issue we had was ordering room service! Too late for food from restaurant, but couldn't order room service until 11pm, we ordered an deliveroo in the end!

Reviewed on Mar 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=1178290&PinnedHotelID=1178290&HadPinnedHotel=true&regionId=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 $96

CA $115 total

Mar 8 - Mar 9

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

Room clean and basic. No drawer or wardrobe space so think it is better for no more than a nights stay. We stayed two nights and the bed was comfy and we had a great sleep. However, the bathroom can’t fit two people in it so expect to wait for a space to brush your teeth!

Reviewed on Mar 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=42101688&PinnedHotelID=42101688&HadPinnedHotel=true&regionId=3000381484)

[See all 2,728 properties in Winsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F03%2F2026&endDate=06%2F03%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

![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)

![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)

[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 rentals near Paultons Family Theme Park - Home of Peppa Pig World ](https://www.expedia.ca/Car-Rentals-In-Paultons-Family-Theme-Park-Home-Of-Peppa-Pig-World.d553248621562854464.Car-Rental-Guide)
- [Car rental Romsey ](https://www.expedia.ca/Car-Rentals-In-Romsey.d5671.Car-Rental-Guide)
- [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. Savings not available on all packages.

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