Book Exclusive Winsor Vacation Packages

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Winsor flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Bournemouth East Cliff Hotel, Sure Hotel Collection by BW

Bournemouth East Cliff Hotel, Sure Hotel Collection by BW

3 out of 5
Bournemouth City Centre
Price was CA $1,615, price is now CA $1,339 per person
CA $1,339
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Southampton (SOU)
Book a stay at this beach hotel in Bournemouth. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bournemouth Beach and Poole Harbour are located nearby.
Bournemouth Carlton Hotel, BW Signature Collection

Bournemouth Carlton Hotel, BW Signature Collection

3 out of 5
Bournemouth City Centre
Price was CA $1,754, price is now CA $1,423 per person
CA $1,423
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Southampton (SOU)
Book a stay at this beach hotel in Bournemouth. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bournemouth Beach and Poole Harbour are located nearby.
Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Price was CA $1,503, price is now CA $1,431 per person
CA $1,431
per person
Apr 2 - Apr 8
just found
Roundtrip non-stop flight included
Calgary (YYC) 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.

Popular places to visit

Southampton Cruise Terminal

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 entertainment choices.

Southampton Cruise Terminal
University of Southampton

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 top-notch restaurants.

University of Southampton
Mayflower Theatre which includes signage and theatre scenes

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.

Mayflower Theatre

Frequently asked questions

How much are vacation packages to Winsor?
Travelocity provides package deals to Winsor, including hotels and flights, starting at just CA $1,339. 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.

Photos of local treasures

Browse Winsor vacation photos for more inspiration

Enclosure on Copythorne Common. Copythorne Common was once part of the New Forest's adjacent commons, but was annexed when the Forest's perambulation was fenced and gridded in the 1960s. The Common is now privately owned, but a portion of it north of the M27 motorway is Access Land. On the left of this photo is the southern edge of a four-sided enclosure defined by a bank and external ditch (marked on the OS 1:25000 Explorer map). Mature oak trees are growing on the bank, showing that the enclosure is at least a few hundred years old.
Enclosure on Copythorne Common. Copythorne Common was once part of the New Forest's adjacent commons, but was annexed when the Forest's perambulation was fenced and gridded in the 1960s. The Common is now privately owned, but a portion of it north of the M27 motorway is Access Land. On the left of this photo is the southern edge of a four-sided enclosure defined by a bank and external ditch (marked on the OS 1:25000 Explorer map). Mature oak trees are growing on the bank, showing that the enclosure is at least a few hundred years old.
Copythorne Church of England Infant School The school viewed from the Scout field.
Photo by ValP (Creative Commons Attribution-Share Alike 2.0)
Fields and hedgerow. Still some good hedgerows in this area. Very nice cycling route into the New Forest from Southampton.
Photo by Footprints (Creative Commons Attribution-Share Alike 2.0)
Oak trees on enclosure bank, Copythorne Common This earthwork is the southern side of a four-sided enclosure defined by a bank and external ditch. Mature oak trees are growing on the bank, showing that the enclosure is at least a few hundred years old.