Winsor Vacations 2026 from CA $1,020

Winsor flight + hotel packages

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

Best Western Chilworth Manor Hotel

CA $1,020

per person

Feb 17 - Feb 20

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Southampton (SOU)

Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southampton Cruise Terminal and Paultons Family Theme Park - Home of Peppa Pig World are located nearby.

Winchester Wessex Hotel by Sunday

CA $1,538

per person

Apr 1 - Apr 8

found 18 hours ago

Roundtrip flight included

Halifax (YHZ) to Southampton (SOU)

Book a stay at this 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 Christmas Market and Winchester Guildhall are located nearby.

No.4 Carlton Hotel

The Polygon

CA $1,371

per person

Feb 17 - Feb 20

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Southampton (SOU)

Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and an airport shuttle (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Southampton Cruise Terminal and Southampton City Art Gallery are located nearby.

Bartley Lodge Hotel

CA $1,096

per person

Feb 17 - Feb 20

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Southampton (SOU)

Book a stay at this business-friendly hotel in Southampton. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions New Forest National Park and Paultons Family Theme Park - Home of Peppa Pig World are located nearby.

The Bitterne Park Hotel

CA $1,243

per person

Feb 17 - Feb 20

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Southampton (SOU)

Stay at this hotel in Southampton. Enjoy free parking, daily housekeeping, and a garden. Popular attractions Southampton Cruise Terminal and Riverside Park are located nearby.

Top Winsor hotels deals

Moxy Southampton

Harbour Parade Southampton England

Free cancellation

Reserve now, pay when you stay

CA $79

CA $95 total

Jan 18 - Jan 19

includes taxes & fees

Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southampton Cruise Terminal and The Quays are located nearby.

Pet-friendly

Free WiFi

Leonardo Hotel Southampton

1 Charlotte Place Southampton England

Free cancellation

Reserve now, pay when you stay

CA $95

CA $114 total

Jan 16 - Jan 17

includes taxes & fees

Book a stay at this business-friendly 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 Southampton Guildhall are located nearby.

Free WiFi

Restaurant

Novotel Southampton

1 West Quay Road Southampton England

Free cancellation

Reserve now, pay when you stay

CA $83

CA $99 total

Feb 1 - Feb 2

includes taxes & fees

Book a stay at this business-friendly 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 Grosvenor Casino are located nearby.

Pet-friendly

Free WiFi

Village Hotel Southampton Eastleigh

Bournemouth Road Eastleigh England

Free cancellation

Reserve now, pay when you stay

Get rates

Book a stay at this business-friendly hotel in Eastleigh. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southampton Cruise Terminal and Southampton City Golf Course are located nearby.

Pool

Hot tub

Leonardo Royal Southampton Grand Harbour

West Quay Road Southampton England

Free cancellation

Reserve now, pay when you stay

CA $109

CA $131 total

Jan 18 - Jan 19

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 Old City Walls are located nearby.

Pool

Spa

Harbour Hotel Southampton

5 Maritime Walk Southampton England

Free cancellation

CA $222

CA $267 total

Jan 18 - Jan 19

includes taxes & fees

Book a stay at this 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 Ocean Village Marina 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

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

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 lively bars.

Mayflower Theatre

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 $1,020. 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.