Windsor Vacations from $995

Book a Hotel + Flight or Car together to unlock savings

Your Windsor Vacation

Lock in a Windsor vacation package that includes everything you need and no unnecessary extras. Good for hiking, adventure sports and golfing, think about staying in the neighborhood of Brookwood. You'll want to do a little exploring during your trip to Windsor. Make time for famous attractions like Windsor Castle, LEGOLAND® Windsor and Frogmore House. Stop dreaming and start traveling. Check out the multitude of options on Expedia today and put your Windsor vacation plans into action!

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Charles Hope London Battersea

Charles Hope London Battersea

3 out of 5
Wandsworth
Price was $1,549, price is now $995 per person
$995
per person
Nov 27 - Nov 30
found 15 hours ago
Roundtrip flight included
New York (JFK) to London (LHR)
8/10 Very Good! (1 review)
Construction next building

Reviewed on Sep 2, 2025

Maddox Street - 3 bed

Maddox Street - 3 bed

2 out of 5
London City Centre
Save 100% on your flight
Price was $4,235, price is now $2,690 per person
$2,690
per person
Dec 14 - Dec 18
just found
Roundtrip flight included
New York (NYC) to London (LHR)
No reviews
Claverley Court

Claverley Court

5 out of 5
London City Centre
Save 100% on your flight
Price was $3,237, price is now $2,160 per person
$2,160
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to London (LHR)
9/10 Wonderful! (63 reviews)
Clean and comfortable property. Great location. Friendly staff. Would highly recommend.

Reviewed on May 16, 2025

1 Bed Serviced Apartment near Blackfriars

1 Bed Serviced Apartment near Blackfriars

4 out of 5
London City Centre
Save 100% on your flight
Price was $1,837, price is now $1,234 per person
$1,234
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to London (LHR)
8/10 Very Good! (4 reviews)
The location was great. The building was fine. The unit was bare-bones in terms of furnishings and tableware (just two bowls) with no personal touch. The shower had serious damage, with tiles bowing out and ready to fall off soon (with water damage to the drywall occurring with every shower, no doubt). It was also hard to get in, as the code sent to me didn't work and it took multiple calls and about 20 minutes of aggravation to get in.

Reviewed on Apr 24, 2025

The Beaumont Mayfair

The Beaumont Mayfair

5 out of 5
London City Centre
Save 100% on your flight
Price was $3,171, price is now $2,134 per person
$2,134
per person
Nov 21 - Nov 25
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)
9.8/10 Exceptional! (262 reviews)
Great hotel and great Lo

Reviewed on Sep 26, 2025

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Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Windsor Castle showing heritage architecture and a castle

Windsor City Centre

5/5(71 area reviews)

Tour the heart of a tranquil riverside city, home to a 1,000-year-old castle where Queen Elizabeth II likes to relax.

Find hotels in Windsor City Centre

Discover the most popular places to visit in Windsor

May 2004 A visit to Legoland in Windsor. A great day out with loads to see and do.

LEGOLAND® Windsor

Enjoy the excitement at LEGOLAND® Windsor and see why this is a favorite theme park in Windsor. Amble around the area's riverfront or seek out the golf courses.

LEGOLAND® Windsor
Windsor Castle showing heritage architecture and a castle

Windsor Castle

Manicured gardens stretch beyond the Gothic turrets of the world’s oldest and largest inhabited castle, a weekend home to royals.

Windsor Castle
Some new cool graffiti in Windsor

Windsor Racecourse

Catch an event at Windsor Racecourse, and enjoy other activities in Windsor such as golfing. Wander the area's riverfront or simply enjoy one of its lively bars.

Windsor Racecourse

What to do in Windsor

sunset at Windsor Castle in London

Windsor Castle Admission Tickets

$42
per adult
78% of travellers recommend
Windsor Castle Admission Tickets
Windsor Castle, Stonehenge and Bath Day Tour with Lunch Pack

Windsor Castle, Stonehenge and Bath Day Guided Tour from London

$121
per adult
86% of travellers recommend
Windsor Castle, Stonehenge and Bath Day Guided Tour from London
Courtesy of English Heritage

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

$272
per adult
88% of travellers recommend
Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor
See all activities in Windsor

Windsor Hotel Deals

Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

4 out of 5
Thames Street, Windsor, England
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $208 total per night from Oct 24 to Oct 25
$208 total
Oct 24 - Oct 25
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
"I have stayed in countless hotels over the years but The Sir Christopher Wren has to be one of the best . The location was perfect, all of the staff were friendly and helpful and the food both at breakfast and for evening meals was top quality. I can`t find a single thing I wasn`t happy with. Dave ..."

Reviewed on Sep 21, 2025

Sir Christopher Wren Hotel
De Vere Beaumont Estate

De Vere Beaumont Estate

4 out of 5
Burfield Road, Berkshire, Windsor, England
$90 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
"Rooms were clean and property was beautiful. Not much options to eat on property but UberEats options were helpful. Accessible property! Very beautiful inside and out."

Reviewed on Oct 1, 2025

De Vere Beaumont Estate
Castle Hotel Windsor

Castle Hotel Windsor

4 out of 5
18 High Street, Windsor, England
$128 nightly
The price is $154 total per night from Oct 16 to Oct 17
$154 total
Oct 16 - Oct 17
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Amazing history in this hotel and right in the heart of Windsor. If you’re planning a visit to the castle this is a must stay."

Reviewed on Oct 2, 2025

Castle Hotel Windsor
See all 531 properties in Windsor
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.

Windsor Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Heathrow Airport (LHR)
Population
33,300
Max Temp Winter
45ºF
Max Temp Summer
70ºF
Top Sights
Windsor Castle, LEGOLAND® Windsor and Theatre Royal

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $995 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
If you'd like to snag a cheap Windsor vacation package, consider planning a trip in November, December and January. You'll typically find lower prices on flights and accommodations during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Windsor?
To get the most out of a Windsor vacation, we suggest staying for 2 days. Split your time between discovering Theatre Royal, Changing of the Guard and other major sights, in addition to exploring neighborhoods like Windsor City Centre and Wexham. If you've got some time to spare, add a tour or day trip to your Windsor vacation itinerary.
Is it worth booking a vacation package to Windsor?
Windsor has everything you need for an awesome getaway — family-friendly attractions, walking trails and history are just the start. Whether you want to check out attractions such as Windsor Castle and LEGOLAND® Windsor, or venture off the beaten track, you'll find plenty to do on your Windsor vacation.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Windsor package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Windsor getaway off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your Windsor retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windsor?
If you've got your Windsor travel dates finalized, book as soon as you can to snap up some outstanding deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Windsor?

  1. Pick your dates: What you want to do in Windsor and your favorite season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodations will likely be the biggest expense during your trip to Windsor.
  3. Use Expedia's trip planning tool to explore Windsor: Research every aspect of your trip to Windsor with this comprehensive planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Work out your trip length: Think about how much time you want to spend discovering Windsor. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Windsor vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a walking tour, you won't have to worry about missing out on the best Windsor has to offer. Find all the incredible things to do in Windsor with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Your Windsor getaway is meant to be an escape from your daily routine, not a reason for money worries. So to give you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.