Winsor Holidays from £162

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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.
Marwell Hotel Winchester South

Marwell Hotel Winchester South

3 out of 5
Save 100% on your flight
per person
24 Sept - 27 Sept
found 1 day ago
Return flight included
Glasgow (GLA) to Southampton (SOU)
7.6/10 Good! (1,002 reviews)
The internet was sketchy. The staff helped rectify this problem. I like the concept of forest surrounding the bungalows.

Reviewed on 29 Jul 2025

Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Save 100% on your flight
per person
24 Sept - 27 Sept
found 1 day ago
Return flight included
Glasgow (GLA) to Southampton (SOU)
7.4/10 Good! (1,007 reviews)
The evening food was very good

Reviewed on 30 Jul 2025

Norton Park Hotel, Spa & Manor House

Norton Park Hotel, Spa & Manor House

4 out of 5
Save 100% on your flight
per person
24 Sept - 27 Sept
found 5 hours ago
Return flight included
Glasgow (GLA) to Southampton (SOU)
7.8/10 Good! (1,000 reviews)
Bed was comfortable, internet access okay. Great setting. Staff were friendly and helpful. Breakfast was good. Had to ask for the eggs to be replenished. Otherwise a pleasant stay.

Reviewed on 1 Aug 2025

The Seaview Hotel

The Seaview Hotel

3 out of 5
per person
16 Sept - 23 Sept
found 22 hours ago
Return direct flight included
Manchester (MAN) to Southampton (SOU)
9.4/10 Exceptional! (11 reviews)
We booked the hotel for our honeymoon. We booked a premium room which was in the Annex at the back of the hotel we liked this as it was nice and quiet and a very spacious room. The room was clean and very comfortable. We visited the hotel restaurant on our first night and the food was delicious and service good. Breakfast was tasty each morning and all of the staff were polite and courteous. Would recommend.

Reviewed on 18 Jun 2025

Enchanted Manor

Enchanted Manor

5 out of 5
per person
16 Sept - 23 Sept
found 22 hours ago
Return direct flight included
Manchester (MAN) to Southampton (SOU)
9.6/10 Exceptional! (29 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

4 out of 5
1 Charlotte Place, Southampton, England
Fully refundableReserve now, pay when you stay
The price is £66 per night from 10 Aug to 11 Aug
£66
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very Good! (1,181 reviews)
"We were only there for a night in order to be close to the boat. It certainly was adequate for that. There were shops and restaurants nearby, which was great. Security stole. Davidson I can’t unpack Metamucil and suppositories and a shelf that works on boats and I know I need like black pants."

Reviewed on 29 Jul 2025

Leonardo Hotel Southampton
Carrington House Hotel

Carrington House Hotel

3 out of 5
Knyveton Road, Bournemouth, England
Fully refundableReserve now, pay when you stay
The price is £52 per night from 3 Aug to 4 Aug
£52
3 Aug - 4 Aug
includes taxes & fees
6.4/10 (1,001 reviews)
"Breakfast is very good I try next time dinner."

Reviewed on 28 Jul 2025

Carrington House Hotel
ibis budget Southampton Centre

ibis budget Southampton Centre

2.5 out of 5
West Quay Road, Western Esplanade, Southampton, England
Fully refundableReserve now, pay when you stay
The price is £43 per night from 17 Aug to 18 Aug
£43
17 Aug - 18 Aug
includes taxes & fees
7.4/10 Good! (1,001 reviews)
"Very nice staff. My check in was very fast"

Reviewed on 31 Jul 2025

ibis budget Southampton Centre
See all 2,838 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

Popular places to visit

Southampton Cruise Terminal

Southampton Cruise Terminal

4.5/5(216 reviews)

One of the busiest cruise ports in England is just a few steps from the historical and entertainment attractions of Southampton.

Southampton Cruise Terminal
University of Southampton

University of Southampton

4/5(55 reviews)

Tour an oceanographic research institute, watch independent theater productions and see designs by notable British architects at this 150-year-old university.

University of Southampton
Mayflower Theatre showing signage and theatre scenes

Mayflower Theatre

4.5/5(49 reviews)

From touring West End musicals to magic shows, stand-up comedy to children’s entertainment, this historic theater serves up Southampton’s best entertainment.

Mayflower Theatre

What to do in Winsor

Courtesy of English Heritage

Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor

£197
per adult
88% of travellers recommend
Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor
Southampton: Guided Ghost Walk

The Southampton Ghost Walk

£15
per adult
100% of travellers recommend
The Southampton Ghost Walk
Portsmouth: Old Portsmouth Historical Walking Tour

Portsmouth: Old Portsmouth Historical Walking Tour

£10
per adult
Portsmouth: Old Portsmouth Historical Walking Tour
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.