Old Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Tristan Young

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Old Windsor Vacation

Say farewell to planning worries and hello to a Old Windsor vacation package. With the finer details organized before you take off, you can focus on discovering this city, starting with Brookwood, which is great for hiking, adventure sports and golfing. If sightseeing is part of the plan during your trip to Old Windsor, stop by leading attractions like Windsor Castle, LEGOLAND® Windsor and Frogmore House. Stop daydreaming and start adventuring. Explore the wide range of options on Expedia today and put your Old Windsor vacation plans into gear!

Top Holiday Package Deals in Old Windsor

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott London Tower Bridge

Residence Inn by Marriott London Tower Bridge

4 out of 5
London City Centre
Price was CA $2,513, price is now CA $1,696 per person
CA $1,696
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to London (LHR)
8.4/10 Very good! (999 reviews)
Breakfast is excellent and good varieties. Need to have a sofa or a few lounge chairs at the reception area for guest to sit around while waiting for friends or share ride

Reviewed on Oct 24, 2026

Hotel Riu Plaza London The Westminster

Hotel Riu Plaza London The Westminster

4 out of 5
London City Centre
Save 100% on your flight
Price was CA $3,093, price is now CA $1,903 per person
CA $1,903
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to London (LHR)
9/10 Wonderful! (2,192 reviews)

Residence Inn by Marriott London Kensington

Residence Inn by Marriott London Kensington

4 out of 5
London City Centre
Price was CA $2,545, price is now CA $1,708 per person
CA $1,708
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to London (LHR)
8.6/10 Excellent! (1,369 reviews)
Breakfast was cold and the room was very very busy . But it was half term so lots of kids . I think it would be better when the kids are in school. The lifts are very slow so you have to wait some time for them to.

Reviewed on Oct 28, 2026

Farringdon Residence

Farringdon Residence

2 out of 5
London City Centre
Save 100% on your flight
Price was CA $3,170, price is now CA $2,208 per person
CA $2,208
per person
Dec 9 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to London (LHR)
No reviews

Edward Hotel Paddington

Edward Hotel Paddington

3.5 out of 5
London City Centre
Save 100% on your flight
Price was CA $3,339, price is now CA $2,347 per person
CA $2,347
per person
Dec 2 - Dec 7
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
7.6/10 Good! (782 reviews)

Where to stay in Old Windsor

Find the best Old Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Old Windsor
A historic stone castle with multiple towers and arched windows.

Windsor City Centre

1 out of top 10 points of interest in this area

The lively bars and stunning river views are top of the list for many visitors to Windsor City Centre. A stop by Windsor Royal Shopping Centre or Windsor Guildhall might round out your trip.

Find hotels in Windsor City Centre

Old Windsor Hotel Deals

Royal Garden Hotel

Royal Garden Hotel

5 out of 5
2-24 Kensington High Street London England
Fully refundableReserve now, pay when you stay
The price is CA $503 per night from Nov 1 to Nov 2
CA $503
CA $604 total
Nov 1 - Nov 2
includes taxes & fees
Royal Garden Hotel
St. James' Court, A Taj Hotel, London

St. James' Court, A Taj Hotel, London

4 out of 5
54 Buckingham Gate London England
Fully refundableReserve now, pay when you stay
The price is CA $436 per night from Nov 8 to Nov 9
CA $436
CA $523 total
Nov 8 - Nov 9
includes taxes & fees
9/10 Wonderful! (1,633 reviews)
"Great hotel, would stay again"

Reviewed on Oct 28, 2026

St. James' Court, A Taj Hotel, London
Sofitel London Heathrow

Sofitel London Heathrow

5 out of 5
Terminal 5 West Drayton England
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Nov 7 to Nov 8
CA $232
CA $279 total
Nov 7 - Nov 8
includes taxes & fees
8.8/10 Excellent! (5,129 reviews)
"This airport hotel is so much better than most airport hotels. Nice rooms and bathrooms, great bar and restaurants. Guests should note that many of the rooms fact inward towards the lobby. If you are a person who has to see out, you should request those rooms."

Reviewed on Oct 28, 2026

Sofitel London Heathrow
See all 18,054 properties in Old 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Old Windsor vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,696 on Expedia. But how much your vacation to Old Windsor costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Old Windsor?
February, April and November are great times to look for cheap Old Windsor vacation packages. Travelling in quieter periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Old Windsor?
Usually, a handful of days is enough for an Old Windsor vacation. With a well-planned itinerary, you can check out all the major sights such as Frogmore House, as well as discover some hidden gems along the way.
Is it worth booking a vacation package to Old Windsor?
Old Windsor offers everything you need for an unforgettable getaway. Get your Old Windsor vacation off to a flying start by checking out top attractions like Windsor Great Park.
How to find the best Old Windsor package deals?
Use Expedia's filter tool to help you find some of the best Old Windsor package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Old Windsor package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Old Windsor vacation as a package?
You can enjoy significant savings on your Old Windsor retreat by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Old Windsor?
If you're considering a spur-of-the-moment Old Windsor vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Old Windsor?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Old Windsor.
  2. Plan your budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Old Windsor.
  3. Decide how long to go away for: Now that you're more familiar with Old Windsor, you can work out the right length of your break. Put together a draft itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Old Windsor vacation package.

Stay near popular Old Windsor attractions

Windsor Great Park

9.4/10 (152 reviews)
Explore the lovely green spaces of Windsor Great Park and enjoy the golf courses in Windsor. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Things to do

LEGOLAND® Windsor Resort Tickets

LEGOLAND® Windsor Resort Tickets

CA $60
per traveller
74% of travellers recommend
LEGOLAND® Windsor Resort Tickets
Windsor Castle, Stonehenge and Bath Day Guided Tour from London

Stonehenge, Windsor Castle and Bath, Day Guided Tour from London

CA $149
per adult
86% of travellers recommend
Stonehenge, Windsor Castle and Bath, Day Guided Tour from London
From Oxford: Cotswolds Towns and Villages Small Group Tour

From Oxford: Cotswolds Towns and Villages Small Group Tour

CA $160
per adult
90% of travellers recommend
From Oxford: Cotswolds Towns and Villages Small Group Tour
See all activities in Windsor
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.