Winsor Holidays

Photo by Jim Champion

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Top hotels in Winsor

Leonardo Hotel Southampton
Leonardo Hotel Southampton
4 out of 5
1 Charlotte Place, Southampton, England
Fully refundable
The price is S$112 per night from 13 Jul to 14 Jul
S$112
13 Jul - 14 Jul
includes taxes & fees
8.4/10 Very Good! (1,155 reviews)
"We’ve stayed at this property a few times now. We like it here as it’s really convenient for a night out in Southampton. Just a quick walk through a lovely park and you are in the heart of the city, convenient for the many pubs, bars restaurants and shops. Southampton guildhall and the Mayflower ..."

Reviewed on 16 Jun, 2025

Leonardo Hotel Southampton
The Winchester Hotel & Spa
The Winchester Hotel & Spa
4 out of 5
Worthy Lane, Winchester, England
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,004 reviews)
"Some of the interiors are dated"

Reviewed on 15 Jun, 2025

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The Winchester Hotel & Spa
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 S$83 per night from 6 Jul to 7 Jul
S$83
6 Jul - 7 Jul
includes taxes & fees
7.6/10 Good! (1,011 reviews)
"affordable"

Reviewed on 17 Jun, 2025

ibis budget Southampton Centre
See all 2,850 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.

Frequently asked questions

How much does a Winsor holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday to Winsor costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Winsor?
You can usually find lower rates and better availability in January, February and November. Check out our cheap Winsor holiday packages and you could score some excellent off-season deals.
How many days is enough for Winsor?
With a well-organised travel plan, you can easily tick off the top Winsor attractions in a few days. But if you prefer to discover hidden gems or take day trips, consider booking your Winsor holiday for longer.
How to find the best Winsor package deals?
Begin your search for a Winsor package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Winsor package deal right away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winsor adventure off to a flying start.
Is it cheaper to book a Winsor holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalised Winsor holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Winsor?
Secure incredible discounts by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Winsor holiday.
How to plan a trip to Winsor?

  1. Choose when to travel: Check your schedule and pack your bags. Your preferred season and the activities available will also help you decide when to escape to Winsor.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to put aside for your trip to Winsor. Then, pick a property that fits your budget, whether that's a wallet-friendly option or a swankier getaway.
  3. Decide your trip length: Think about how long you'd like to spend exploring Winsor. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customised Winsor holiday package.

Popular places to visit

Mayflower Theatre which includes signage and theatre scenes

Mayflower Theatre

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
Exbury Gardens and Steam Railway

Exbury Gardens and Steam Railway

All aboard for a classic steam railway journey through gorgeous Hampshire woodlands and colorful flower displays packed with fascinating and rare blooms.

Exbury Gardens and Steam Railway
Netley Abbey

Netley Abbey

Find out about the history of Southampton with a stop at Netley Abbey. Wander the lush forest and waterfront in the area.

Netley Abbey

What to do in Winsor

Stonehenge Tour from Southampton to London

Stonehenge Tour from Southampton to London

S$228
per adult
100% of travellers recommend
Stonehenge Tour from Southampton to London
Courtesy of English Heritage

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

S$289
per adult
86% of travellers recommend
Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor
Walk the Secrets of the Titanic

Walk the Secrets of the Titanic

S$28
per adult
100% of travellers recommend
Walk the Secrets of the Titanic
See all activities in Winsor

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.