
Windsor and Maidenhead Vacations & Trips from $1,065
Book a Hotel + Flight or Car together to unlock savings
The Latest Windsor and Maidenhead Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Staines City Centre by Charles Hope
Staines Town Centre
Save 100% on your flight
Price was $1,648, price is now $1,065 per person
$1,065
per person
Oct 30 - Nov 11
found 13 hours ago
Roundtrip flight included
Boston (BOS) to London (LHR)
8.8/10 Excellent! (35 reviews)
Nice and spacious apartment, I love it!
Reviewed on Jul 7, 2025

Charles Hope Apartments Brentford
Save 100% on your flight
Price was $1,965, price is now $1,221 per person
$1,221
per person
Oct 30 - Nov 11
found 13 hours ago
Roundtrip flight included
Boston (BOS) to London (LHR)
8.6/10 Excellent! (69 reviews)
Had a pleasant stay, Spacious,Clean and Comfortable apartments. Friendly and helpful staff.
Reviewed on Aug 22, 2025

Staines Riverside by Charles Hope
Save 100% on your flight
Price was $1,841, price is now $1,160 per person
$1,160
per person
Oct 30 - Nov 11
found 13 hours ago
Roundtrip flight included
Boston (BOS) to London (LHR)
7.6/10 Good! (13 reviews)
Lovely apartment, only downfalls was the floor was dirty and hadn’t been cleaned, one of the beds sheets had staines of some sort. Beds were uncomfortable and the parking opposite only allows you to book until 12 midnight, you then have to wake up at 6am to pay again as there’s no option to pay for 24hrs obviously this has nothing to do with the owners but something to be aware when booking.
Reviewed on Dec 1, 2024

Windsor and Maidenhead Hotel Deals

De Vere Beaumont Estate
Burfield Road, Berkshire, Windsor, England
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $152 total per night from Aug 31 to Sep 1
$152 total
Aug 31 - Sep 1
Total with taxes and fees

Sir Christopher Wren Hotel
Thames Street, Windsor, England
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $209 total per night from Sep 7 to Sep 8
$209 total
Sep 7 - Sep 8
Total with taxes and fees

Castle Hotel Windsor
18 High Street, Windsor, England
$125 nightly
The price is $150 total per night from Aug 31 to Sep 1
$150 total
Aug 31 - Sep 1
Total with taxes and fees
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.
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Windsor and Maidenhead
- Vacations and getaways similar to Windsor and Maidenhead
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.