Winsor Vacations 2025/2026 from CA $1,386

Winsor flight + hotel packages

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

Apollo Hotel

CA $1,386

per person

Dec 25 - Dec 30

found 2 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Southampton (SOU)

Book a stay at this spa hotel in Basingstoke. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions The Anvil and Festival Place are located nearby.

No.4 Carlton Hotel

The Polygon

CA $4,196

per person

Dec 28 - Jan 2

found 10 hours ago

Roundtrip flight included

Halifax (YHZ) 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.

Southampton retreat-Hot Tub-Pool-Parking

Shirley

CA $4,959

per person

Dec 28 - Jan 2

found 10 hours ago

Roundtrip flight included

Halifax (YHZ) to Southampton (SOU)

Stay at this apartment in Southampton. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Southampton Cruise Terminal and Paultons Family Theme Park - Home of Peppa Pig World are located nearby.

Southampton Serviced Apartment

Bassett

CA $3,759

per person

Dec 28 - Jan 2

found 10 hours ago

Roundtrip flight included

Halifax (YHZ) to Southampton (SOU)

Book a stay at this business-friendly apartment in Southampton. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Southampton Cruise Terminal and The Common are located nearby.

Bartley Lodge Hotel

CA $3,674

per person

Dec 28 - Jan 2

found 10 hours ago

Roundtrip flight included

Halifax (YHZ) 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.

Top Winsor hotels deals

Moxy Southampton

Harbour Parade Southampton England

Free cancellation

Reserve now, pay when you stay

CA $90

CA $108 total

Dec 7 - Dec 8

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 $96

CA $116 total

Nov 30 - Dec 1

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

Leonardo Royal Southampton Grand Harbour

West Quay Road Southampton England

Free cancellation

Reserve now, pay when you stay

CA $122

CA $147 total

Nov 30 - Dec 1

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

Village Hotel Southampton Eastleigh

Bournemouth Road Eastleigh England

Free cancellation

Reserve now, pay when you stay

CA $95

CA $114 total

Nov 23 - Nov 24

includes taxes & fees

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

Novotel Southampton

1 West Quay Road Southampton England

Free cancellation

Reserve now, pay when you stay

CA $91

CA $109 total

Dec 7 - Dec 8

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

The Winchester Hotel & Spa

Worthy Lane Winchester England

Free cancellation

Reserve now, pay when you stay

Get rates

Book a stay at this 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 Theatre Royal Winchester and Westgate Museum are located nearby.

Pool

Hot tub

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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.

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.

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 lively bars.

Frequently asked questions

How much are vacation packages to Winsor?

Travelocity provides package deals to Winsor, including hotels and flights, starting at just CA $1,386. 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.