Winsor Vacations 2025/2026 from CA $886

Winsor flight + hotel packages

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

Macdonald Botley Park Hotel & Spa

per person

Oct 3 - Oct 5

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Southampton (SOU)

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 Utilita Bowl are located nearby.

Winchester Wessex Hotel by Sunday

per person

Aug 26 - Sep 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Southampton (SOU)

Stay at this 4-star business-friendly hotel in Winchester. 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 Winchester Cathedral and Winchester Christmas Market are located nearby.

Belvilla Russel Court Hotel Bournemouth Central

Bournemouth City Centre

per person

Aug 21 - Aug 27

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Southampton (SOU)

Stay at this hotel in Bournemouth. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Poole Harbour and Bournemouth Beach are located nearby.

Holiday Inn Farnborough by IHG

Rushmoor District

per person

Aug 17 - Aug 23

found 16 hours ago

Roundtrip flight included

Montreal (YUL) to Southampton (SOU)

Stay at this 4-star business-friendly hotel in Farnborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Farnborough Air Sciences Trust Museum and Army Golf Club are located nearby.

HQ Aparthotel Farnborough

Rushmoor District

per person

Sep 8 - Sep 12

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Southampton (SOU)

Stay at this 4-star business-friendly aparthotel in Farnborough. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Kingsmead Shopping Centre and St Michaels Abbey are located nearby.

Top Winsor hotels deals

Leonardo Hotel Southampton

1 Charlotte Place, Southampton, England

Free cancellation

CA $97

CA $116 total

Jul 27 - Jul 28

includes taxes & fees

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 budget Southampton Centre

West Quay Road, Western Esplanade, Southampton, England

Free cancellation

Reserve now, pay when you stay

CA $66

CA $79 total

Jul 27 - Jul 28

includes taxes & fees

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

Carrington House Hotel

Knyveton Road, Bournemouth, England

Free cancellation

Reserve now, pay when you stay

CA $80

CA $96 total

Jul 15 - Jul 16

includes taxes & fees

Stay at this 3-star business-friendly hotel in Bournemouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Poole Harbour and Bournemouth Beach are located nearby.

Pool

Pet-friendly

Village Hotel Bournemouth

Wessex Fields, Deansleigh Road, Bournemouth, England

Free cancellation

Reserve now, pay when you stay

CA $132

CA $159 total

Jul 20 - Jul 21

includes taxes & fees

Stay at this 3.5-star eco-certified hotel in Bournemouth. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bournemouth Beach and Bournemouth Pier are located nearby.

Pool

Hot tub

Holiday Inn Express Southampton M27 Jct7 by IHG

Botley Road, West End, Southampton, England

Free cancellation

CA $91

CA $109 total

Jul 27 - Jul 28

includes taxes & fees

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 Royal Southampton Grand Harbour

West Quay Road, Southampton, England

Free cancellation

Reserve now, pay when you stay

CA $139

CA $166 total

Jul 27 - Jul 28

includes taxes & fees

Book a stay at this spa hotel in Southampton. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located nearby.

Pool

Spa

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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 entertainment choices.

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 $886. 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.