Winsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winsor

Carrington House Hotel

Carrington House Hotel

3 out of 5
Knyveton Road, Bournemouth, England
Fully refundableReserve now, pay when you stay
The price is 1.396.395 ₫ per night from 7 Sept to 8 Sept
1.396.395 ₫
1.675.674 ₫ total
7 Sept - 8 Sept
includes taxes & fees
6.4/10 (1,002 reviews)
Good for a short stay
"Good for a short stay"

Reviewed on 17 Aug 2025

Carrington House Hotel
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! (1,002 reviews)
"Clean modern Good location Helpful staff"

Reviewed on 22 Aug 2025

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The Winchester Hotel & Spa
Meon Valley Hotel, Golf & Country Club

Meon Valley Hotel, Golf & Country Club

4 out of 5
Sandy Lane, Shedfield, Southampton, England
Fully refundableReserve now, pay when you stay
The price is 2.039.001 ₫ per night from 25 Aug to 26 Aug
2.039.001 ₫
2.446.801 ₫ total
25 Aug - 26 Aug
includes taxes & fees
6.8/10 (1,004 reviews)
"Molly on reception excellent!"

Reviewed on 22 Aug 2025

Meon Valley Hotel, Golf & Country Club
See all 2,837 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.

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
Mayflower Theatre showing signage and theatre scenes

Mayflower Theatre

Enjoy a performance at Mayflower Theatre, a theatre with a story to tell in Southampton. Experience the area's entertainment choices and acclaimed theatre scene.

Mayflower Theatre
Mayflower Park

Mayflower Park

Mayflower Park is just one of the places to see in Southampton, so why not enjoy the other things to explore during your travels? Wander around the area's the lush forest or experience its entertainment choices.

Mayflower Park

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.