Windsor and Maidenhead Vacations & Trips from $1,065

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 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

The Latest Windsor and Maidenhead Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Staines City Centre by Charles Hope
Charles Hope Apartments Brentford
Staines Riverside by Charles Hope
One Bed Serviced Apartment in Chelsea
Maddox Street - 3 bed

Windsor and Maidenhead Hotel Deals

De Vere Beaumont Estate

De Vere Beaumont Estate

4 out of 5
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
De Vere Beaumont Estate
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 $209 total per night from Sep 28 to Sep 29
$209 total
Sep 28 - Sep 29
Total with taxes and fees
Sir Christopher Wren Hotel
Castle Hotel Windsor

Castle Hotel Windsor

4 out of 5
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
Castle Hotel 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.