Winsor Holidays from £236

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Your Winsor Holiday

Reserve a Winsor holiday package that has everything you need without any unnecessary extras. Great for dining, cafes and bars and pubs, consider basing yourself in the neighbourhood of Southampton City Centre. You'll want to go sightseeing during your trip to Winsor. Find time for major attractions such as New Forest Wildlife Park, The Common and Romsey Golf Club. Stop dreaming and start travelling. Explore the multitude of options on Expedia today and put your Winsor holiday plans in motion!

Top Winsor Flight + Hotel Deals

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

Novotel Southampton

Southampton City Centre
£236
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Guernsey (GCI) to Southampton (SOU)
8.2/10 Very good! (1,007 reviews)
Nice Hotel close to port.

Reviewed on 28 Aug 2026

No.4 Carlton Hotel

No.4 Carlton Hotel

The Polygon
£422
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Guernsey (GCI) to Southampton (SOU)
9.6/10 Exceptional! (158 reviews)
We were are the third floor, no elevator. Our room could have ued a magnifying mirror in bathroom, as the mirror was too high for a short person.

Reviewed on 28 Aug 2026

Best Western Chilworth Manor Hotel

Best Western Chilworth Manor Hotel

£241
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Guernsey (GCI) to Southampton (SOU)
8/10 Very good! (1,006 reviews)
A really nice Hotel. Cannot fault on anything. Hotel spotless, staff, very friendly. A pleasurable stay. Thank you.

Reviewed on 25 Aug 2026

QE2 Loft Apartments

QE2 Loft Apartments

Southampton City Centre
£307
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Guernsey (GCI) to Southampton (SOU)
6.4/10 (8 reviews)
Hotel Haveli Ltd.

Hotel Haveli Ltd.

£338
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Guernsey (GCI) to Southampton (SOU)
No reviews

Winsor Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southampton Airport (SOU)
Max Temp Winter
7ºC
Max Temp Summer
21ºC
Top Sights
Mayflower Theatre, New Forest Wildlife Park and Solent Sky Museum

Top hotels in Winsor

Leonardo Hotel Southampton

Leonardo Hotel Southampton

1 Charlotte Place Southampton England
Fully refundableReserve now, pay when you stay
£70
7 Sept - 8 Sept
includes taxes & fees
Leonardo Hotel Southampton
Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

West Quay Road Southampton England
Fully refundableReserve now, pay when you stay
£100
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (1,803 reviews)
"Stay was great. Very close to port for cruise. Only one issue, but it was not with the hotel. Concierge scheduled us a taxi for travel to port, literally 6 blocks away. Taxi charged us $20. It was 2 people & 2 medium suitcases, and 2 backpacks that we kept with us. Definitely would recommend using ..."

Reviewed on 28 Aug 2026

Leonardo Royal Southampton Grand Harbour
Meon Valley Hotel, Spa & Golf

Meon Valley Hotel, Spa & Golf

Sandy Lane Southampton England
Fully refundableReserve now, pay when you stay
£59
31 Aug - 1 Sept
includes taxes & fees
Meon Valley Hotel, Spa & Golf
See all 3,130 properties in Winsor
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.

The Advantages of Winsor Weekend Breaks

Discover a different side of the British Isles with a weekend break in Winsor. Take short breaks away from home and enjoy some quality time in a beautiful place. You’ll come back feeling refreshed and inspired. You can have an action-packed Winsor weekend break or get some peace with a relaxing holiday. Whatever experience you’re looking for, find it with our deals on hotels in Winsor.

Cheap Weekend Breaks to Winsor

There are lots of ways to take cheap weekend breaks to Winsor. Expedia offers deals on car hires and hotel rooms and covers trips for all kinds of travellers. The best way to save is with our holiday packages in Winsor. First, choose your car hire and hotel reservation. Then we’ll bundle them together into one discounted price. Solo explorers, couples, families, and groups of friends can discover budget solutions for their weekend breaks. Once you arrive, enjoy some of the fun things to do, many of which are free or cheap to experience  

Winsor Romantic Weekend Breaks

Couples love taking romantic weekend breaks in Winsor. Whisking your lover away for a romantic Winsor weekend break is the perfect opportunity to make new memories together. Expedia offers all kinds of hotel options, so you can find romantic hotels in Winsor and choose the best place for you. Check out our deals on beautiful properties, and you’ll save even more when you choose to package your hotel reservation with a car hire.

Family Weekend Breaks in Winsor

Set some time aside to experience family weekend breaks in Winsor. There are plenty of excellent family-friendly hotels in Winsor within our selection of hotels. You can also find a place to call home in one of the holiday rentals in Winsor. With accommodation, activities, and adventure all waiting, there’s never been a better time to plan Winsor family weekend breaks.

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

What to do in Winsor

Isle of Wight: Osborne Admission Ticket

Isle of Wight: Osborne Admission Ticket

£22
per adult
100% of travellers recommend
Isle of Wight: Osborne Admission Ticket
Portsmouth Historic Dockyard Ultimate Explorer Ticket

Portsmouth Historic Dockyard Ticket

£46
per adult
100% of travellers recommend
Portsmouth Historic Dockyard Ticket
Southampton: Guided Ghost Walk

The Southampton Ghost Walk

£15
per adult
100% of travellers recommend
The Southampton Ghost Walk
See all activities in Winsor

Frequently asked questions

Why should I book my Winsor holiday with Expedia?
Choose Expedia to organise your next break easily and all in one convenient place. Our top tip for scoring a fabulous deal on a Winsor getaway? Bundle your flights, accommodation and/or car hire into a package holiday. Then add a couple of fun tours and activities. Many bookings also have flexible cancellation policies, so there's no need to panic if you have to switch up your itinerary. Round-the-clock assistance with cancelling and changing your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Winsor?
July, August and September are the busiest months in Winsor, while December, January and February are generally quieter. With daytime average temperatures of 5ºC, January is the coolest period in Winsor. The warmest time of year is July, when you can expect averages of 17ºC throughout the day. Whatever the weather, you'll find a whole lot to keep you occupied here.
What is the top hotel for my holiday in Winsor?
Relax in comfort in Winsor by choosing The Botleigh Grange Hotel as your gateway to exploration and adventure.
How do I get a cheap holiday to Winsor?
Our Winsor holidays promise plenty of savings for the savvy traveller. For the best deal, simply bundle your flights, hotels and hire cars. But great bargains are only the start of your next memorable adventure. When you book with Expedia, you'll have more than 400 airlines and 321,000 hotels globally to choose from. No matter your style or budget, there's a holiday here that's perfect for you. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Winsor holiday?
There are so many things to keep you busy while having a holiday in Winsor. Southampton Maritime Museum, Southampton Cruise Terminal, WestQuay Shopping Centre and University of Southampton are among this city's key attractions.
Do I need a visa for my Winsor holiday?
Visa requirements for Winsor vary depending on your nationality and purpose of your visit. Make sure you check official government websites to determine if you need a visa for your holiday. This is also a good place to find the most up-to-date information, including details about application procedures and any supporting documentation that might be necessary. Research your visa requirements well ahead of time to ensure a smooth travel experience. Also check to see that your passport is valid for at least six months from your planned return date.
What should I wear on my Winsor holiday?
Although everyone's style varies, it can be useful to have some guidelines for what to bring on your holiday in Winsor. We recommend browsing social media before you head off so you can blend in like a local. Take a look at the local weather forecast so you can pack your bags accordingly. The warmest month in Winsor is July, with average daytime temperatures of 17ºC. If you plan to travel during the coolest month of January, the mercury averages 5ºC during the day.
What does an Expedia Winsor holiday include?
It comes down to what sort of trip you're thinking about. Winsor holiday deals can include hotels, car hires and flights. You can mix and match to create the package that suits your needs. You can also add on experiences and activities after you've booked to get even bigger discounts. Cottages and mobile homes are a couple of the most sought-after property types in Winsor. Whatever your preference or size of your group, you can count on Expedia for the freedom and flexibility to tailor your next big adventure.
Does Expedia offer Book Now, Pay Later Winsor holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a terrific getaway without exhausting your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Consider one of these flexible payment options:
  • Pay monthly holidays: Klarna offers payments in multiple transactions that suit all types of budgets, so you can take that well-deserved holiday now.
  • No-deposit holidays: If not paying ahead of time for your getaway makes hitting that "book now" button more stress-free, choose a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!
Can I choose my airline with a Winsor Expedia holiday?
Definitely. Expedia has more than 400 partner airlines to choose from around the world. With such a huge range of choices, finding the ideal carrier to fly you to Winsor will be a cinch.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.