Winsor Vacations 2025 from CA $1,518

Winsor flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Holiday Inn Basingstoke by IHG

per person

Aug 14 - Aug 20

just found

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

Stay at this 4-star business-friendly hotel in Basingstoke. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Willis Museum and Wote Street Willy are located nearby.

Old Thorns Hotel & Resort

per person

Aug 14 - Aug 20

just found

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

Stay at this 4-star spa hotel in Liphook. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Old Thorns Golf Course and Liphook Golf Club are located nearby.

Hampshire Court Hotel & Spa

per person

Aug 14 - Aug 20

just found

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

Stay at this 4-star spa hotel in Basingstoke. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Mill Field Nature Reserves and Basing House are located nearby.

The Jolly Drover

per person

Aug 14 - Aug 20

just found

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

Stay at this 4-star inn in Liss. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Liss Centenary Garden and Liss Forest Recreation Ground are located nearby.

Apple Tree Place B&B

per person

Aug 14 - Aug 20

just found

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

Stay at this 4-star B&B in Tadley. Enjoy free parking, breakfast (surcharge), and daily housekeeping. Popular attractions Bishopwood Golf Club and Silchester Roman City Walls and Amphitheatre are located nearby.

Top Winsor hotels deals

Holiday Inn Express Southampton M27 Jct7 by IHG

Botley Road, West End, Southampton, England

Free cancellation

CA $97

CA $116 total

includes taxes & fees

Jun 8 - Jun 9

Stay at this 3-star eco-certified hotel in Southampton. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.

Breakfast included

Pet-friendly

Leonardo Hotel Southampton

1 Charlotte Place, Southampton, England

Free cancellation

CA $114

CA $136 total

includes taxes & fees

Jun 22 - Jun 23

Stay at this 4-star eco-certified hotel in Southampton. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.

Free WiFi

Restaurant

ibis Southampton Centre

9 West Quay Road, Southampton, England

CA $96

CA $115 total

includes taxes & fees

Jun 30 - Jul 1

Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.

Macdonald Botley Park Hotel & Spa

Winchester Road, Boorley Green, Southampton, England

Free cancellation

Reserve now, pay when you stay

CA $92

CA $111 total

includes taxes & fees

Jun 8 - Jun 9

Stay at this 4-star spa hotel in Southampton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions WestQuay Shopping Centre and Ageas Bowl Cricket Ground are located nearby.

Pool

Spa

Harbour Hotel Southampton

5 Maritime Walk, Ocean Village, Southampton, England

Free cancellation

CA $257

CA $308 total

includes taxes & fees

Jun 8 - Jun 9

Stay at this 5-star luxury hotel in Southampton. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.

Pool

Spa

ibis budget Southampton Centre

West Quay Road, Western Esplanade, Southampton, England

Free cancellation

Reserve now, pay when you stay

CA $72

CA $87 total

includes taxes & fees

Jun 30 - Jul 1

Stay at this hotel in Southampton. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.

Pet-friendly

Free WiFi

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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.

Popular places to visit

Southampton Cruise Terminal

4.5/5(51 reviews)

Explore the waterfront in Southampton with a trip to Southampton Cruise Terminal. Wander around the area's the lush forest or experience its acclaimed theater scene.

University of Southampton

3.5/5(7 reviews)

Enjoy the collegiate vibe when you visit University of Southampton, during your travels in Southampton. Wander the area's lush forest or simply enjoy one of its top-notch restaurants.

Mayflower Theatre

5/5(1 review)

Enjoy a performance at Mayflower Theatre, a theater with a story to tell in Southampton. Experience the area's acclaimed theater scene and entertainment choices.

Frequently asked questions

How much are vacation packages to Winsor?

Travelocity provides package deals to Winsor, including hotels and flights, starting at just CA $1,518. With all the extra cash, you could book some popular tours or perhaps even add a few extra days to your exciting getaway.

Where can I get the best vacation package deals for Winsor?

Travelocity is here to help you snap up an awesome Winsor package deal. With as many as 400 airlines and 1,000,000 properties across the world, you’re bound to find the perfect mix.

Why should I purchase my Winsor vacation bundle via Travelocity?

You’ll not only save lots, but you’ll also have access to our 24/7 support, top-notch service and a Price Match Guarantee. Journey across the world, uncover lesser-known sights and make lifelong memories — we’ll take care of the important details.

Can I save money on my Winsor car rental if I book it with a hotel or flight?

With a Winsor vacation package, you can bundle your hotel, flight and car bookings and save loads. If you want to see the best of this awesome region, why not start with Big Ben? This well-known sight is 121 kilometers from Winsor. With your own wheels, you’ll be there belong long.

Which airport is best for Winsor?

Chances are you’ll touch down at Heathrow Airport (LHR), which is 97 kilometers northeast of downtown Winsor. Bristol Intl. Airport (BRS) (97 kilometers away from central Winsor) and Southampton Airport (SOU) (13 kilometers away from central Winsor) are other options.

Where should I stay when visiting Winsor?

The Lovely cottage & garden. 5 min drive from Paultons Park, home of Peppa Pig is the top choice of many visitors. Book soon to avoid missing out.