Old Windsor Vacations from $995
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Photo by Tristan Young
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!
The Latest Old Windsor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Croydon by Charles Hope
Fairfield
Price was $1,373, price is now $995 per person
$995
per person
Mar 12 - Mar 19
found 14 hours ago
Roundtrip flight included
New York (JFK) to London (LHR)
8.6/10 Excellent! (17 reviews)
Great property in a great location. Apart from a few minor broken things in the unit, it was clean, comfortable and had everything we needed. Will certainly be back!
Reviewed on Jul 4, 2025
Leicester House Hotel
London City Centre
Save 100% on your flight
Price was $1,939, price is now $1,396 per person
$1,396
per person
Apr 16 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)
8.6/10 Excellent! (48 reviews)
Simple hotel (light on amenities), very good location.
Room was very clean, well styled, and comfortable bed. The bath tub/shower are raised up, so for mobility impaired people might be a challenge.
The staff were exceptionally kind and courteous. Truly an outstanding experience.
Reviewed on Dec 1, 2025
Hotel Shepherds Bush London
Hammersmith and Fulham
Price was $1,502, price is now $1,098 per person
$1,098
per person
Mar 12 - Mar 19
found 14 hours ago
Roundtrip flight included
New York (JFK) to London (LHR)
8.2/10 Very Good! (478 reviews)
Clean and comfortable room. Attentive and friendly staff. Good value for the area. Will stay there again.
Reviewed on Jan 24, 2026
Hotel Cafe Royal, London
London City Centre
Save 100% on your flight
Price was $4,208, price is now $3,107 per person
$3,107
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to London (LHR)
9.6/10 Exceptional! (547 reviews)
Beautifully designed room by David Chipperfield Architects-the reason I booked my stay here! The property is historic and well maintained. No matter how wonder the facilities are though, the staff makes or breaks a stay. In this case, the staff made an incredible building even more so with excellent service from the doorman to the front desk staff to the cleaning staff and spa staff. They all took it upon themselves to make sure I was being taken care of during my stay. I am looking forward to a return visit soon!
Reviewed on Jan 20, 2026
Marrable's Farringdon Hotel
London City Centre
Price was $1,966, price is now $1,456 per person
$1,456
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)
9.2/10 Wonderful! (646 reviews)
Great staff - lively room - very comfortable and well run
Reviewed on Jan 27, 2026
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
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.
Old Windsor Hotel Deals
Royal Garden Hotel
2-24 Kensington High Street London England
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $251 total per night from Feb 15 to Feb 16
$251 total
Feb 15 - Feb 16
Total with taxes and fees
9.2/10 Wonderful! (1,838 reviews)
Excellent
Reviewed on Jan 31, 2026
Sofitel London Heathrow
Terminal 5 West Drayton England
Fully refundableReserve now, pay when you stay
$173 nightly
The price is $208 total per night from Feb 16 to Feb 17
$208 total
Feb 16 - Feb 17
Total with taxes and fees
8.8/10 Excellent! (4,915 reviews)
Staff were friendly and helpful and you cannot beat the location if you have an early flight from T5. I was only there for one night but would say that a major miss was that they did not have any plugs bedside. I don't want to have to get out of bed to access my devices.
Reviewed on Feb 3, 2026
Renaissance London Heathrow Hotel
Bath Road Hounslow England
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $122 total per night from Feb 8 to Feb 9
$122 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (2,567 reviews)
Convenient to the airport. Easy check-in. Clean room. Shuttle to the airport.
Reviewed on Jan 31, 2026
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.
Discover the most popular places to visit in Old Windsor
Windsor Great Park
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.
Copper Horse
Find out about the history of Windsor when you spend time at Copper Horse. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Hands-on Art Studio
Enjoy an outing to Hands-on Art Studio during your stay in Windsor. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Things to do
Windsor Castle, Stonehenge and Bath Day Guided Tour from London
$108
per adult
86% of travellers recommend
Day trip to Windsor, Oxford & Stonehenge from London
$119
per adult
80% of travellers recommend
Legoland® Windsor with Roundtrip Transportation
$106
per adult
74% of travellers recommend
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.