Winsor Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Winsor Vacation Packages

Winsor Hotel Deals

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 AED 256 per night from Apr 27 to Apr 28
AED 256
AED 308 total
includes taxes & fees
27 Apr - 28 Apr
8.4/10 Very Good! (1,147 reviews)
"In the middle of a road junction, but the sound insulation is good - while the windows are closed! Comfortable beds, well appointed room."

Reviewed on 15 April 2025

Leonardo Hotel Southampton
Holiday Inn Express Southampton M27 Jct7 by IHG
Holiday Inn Express Southampton M27 Jct7 by IHG
3 out of 5
Botley Road, West End, Southampton, England
Fully refundable
The price is AED 260 per night from Apr 21 to Apr 22
AED 260
AED 313 total
includes taxes & fees
21 Apr - 22 Apr
8.6/10 Excellent! (1,002 reviews)
"Comfort"

Reviewed on 15 April 2025

Holiday Inn Express Southampton M27 Jct7 by IHG
Leonardo Royal Southampton Grand Harbour
Leonardo Royal Southampton Grand Harbour
4 out of 5
West Quay Road, Southampton, England
Fully refundableReserve now, pay when you stay
The price is AED 346 per night from Apr 21 to Apr 22
AED 346
AED 415 total
includes taxes & fees
21 Apr - 22 Apr
8.6/10 Excellent! (1,452 reviews)
Anniversary stay
"Few hairs in bath where not rinsed out properly. Room clean, fresh and very comfortable. Enjoyable hitel, staff excellent, unfortunately spoilt by restaurant, thougn sure it was a one off"

Reviewed on 14 April 2025

Leonardo Royal Southampton Grand Harbour
See all 2,721 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 vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation packages and you could score some excellent off-season deals.
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 vacation as a package?
Expedia vacation 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 personalized Winsor vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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 vacation.
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 customized Winsor vacation package.

Discover the most popular places to visit in Winsor

Southampton Cruise Terminal

Southampton Cruise Terminal

4.5/5(96 reviews)

Explore the waterfront in Southampton with a trip to Southampton Cruise Terminal. Wander around the area's the lush forest or experience its acclaimed theater scene.

Southampton Cruise Terminal
University of Southampton

University of Southampton

4.5/5(21 reviews)

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 featuring signage and theater scenes

Mayflower Theatre

5/5(1 review)

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