Winsor Vacations 2025 from CA $870

Winsor flight + hotel packages

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

HQ Aparthotel Farnborough

Rushmoor District

per person

May 24 - May 28

found 16 hours ago

Roundtrip flight included

St. John's (YYT) 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.

Langtry Manor Hotel

per person

May 19 - May 23

found 7 hours ago

Roundtrip flight included

Halifax (YHZ) to Southampton (SOU)

Stay at this 3.5-star luxury hotel in Bournemouth. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Poole Harbour and Bournemouth Beach are located nearby.

The Cumberland Hotel - OCEANA COLLECTION

Bournemouth City Centre

per person

May 19 - May 23

found 7 hours ago

Roundtrip flight included

Halifax (YHZ) to Southampton (SOU)

Stay at this 4-star beach hotel in Bournemouth. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Poole Harbour and Bournemouth Beach are located nearby.

Hermitage Hotel OCEANA COLLECTION

Bournemouth City Centre

per person

May 19 - May 23

found 7 hours ago

Roundtrip flight included

Halifax (YHZ) to Southampton (SOU)

Stay at this 4-star beach hotel in Bournemouth. Enjoy free WiFi, 2 restaurants, 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.

Suncliff Hotel - OCEANA COLLECTION

Bournemouth City Centre

per person

May 19 - May 23

found 7 hours ago

Roundtrip flight included

Halifax (YHZ) to Southampton (SOU)

Stay at this 3-star beach hotel in Bournemouth. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Poole Harbour and Bournemouth Beach are located nearby.

Top Winsor hotels deals

Leonardo Hotel Southampton

1 Charlotte Place, Southampton, England

Free cancellation

CA $96

CA $116 total

includes taxes & fees

Apr 27 - Apr 28

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

Holiday Inn Express Southampton M27 Jct7 by IHG

Botley Road, West End, Southampton, England

Free cancellation

CA $98

CA $117 total

includes taxes & fees

Apr 21 - Apr 22

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 $130

CA $156 total

includes taxes & fees

Apr 27 - Apr 28

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

The Winchester Hotel & Spa

Worthy Lane, Winchester, England

Free cancellation

Reserve now, pay when you stay

CA $115

CA $138 total

includes taxes & fees

Apr 21 - Apr 22

Stay at this 4-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Winchester Cathedral and Theatre Royal Winchester are located nearby.

Pool

Hot tub

Harbour Hotel Southampton

5 Maritime Walk, Ocean Village, Southampton, England

Free cancellation

CA $246

CA $296 total

includes taxes & fees

May 18 - May 19

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

Moxy Southampton

Harbour Parade, Southampton, England

Free cancellation

Reserve now, pay when you stay

CA $109

CA $130 total

includes taxes & fees

May 18 - May 19

Stay at this 3-star eco-certified hotel in Southampton. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the bar and the helpful staff 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 entertainment choices and acclaimed theater scene.

Frequently asked questions

How much are vacation packages to Winsor?

Travelocity provides package deals to Winsor, including hotels and flights, starting at just CA $870. 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.