The Best Things to Do in Windsor and Maidenhead

Create a fully customized
day-by-day itinerary for free

Itinerary Planner
+ Add destination
2 adults
Adults
- +
Teens
- +
Kids
- +
Close

Plan your trip to Windsor and Maidenhead

  • Get a personalized plan

    A complete day-by-day itinerary
    based on your preferences
  • Customize it

    Refine your plan. We'll find the
    best routes and schedules
  • Book it

    Choose from the best hotels
    and activities. Up to 50% off
  • Manage it

    Everything in one place.
    Everyone on the same page.

Where to stay in Windsor and Maidenhead

Browse hotels, guesthouses, and unique homes and book your stay on the world's leading accommodation sites.
Millions of travel reviews on TripAdvisor
2 adults
Adults (12 +)
- +
Children (2-11)
- +
Infants (Under 2)
- +
Close
Live like a local, find unique places to stay
2 adults
Adults (12 +)
- +
Children (2-11)
- +
Infants (Under 2)
- +
Close

Recently planned trips to Windsor and Maidenhead

4 days in Windsor BY A USER FROM CANADA July, outdoors, relaxing, historic sites, museums, wildlife, hidden gems PREFERENCES: July, outdoors, relaxing, historic sites, museums, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 2 days in Windsor BY A USER FROM CANADA June, culture, outdoors, beaches, historic sites, wildlife, popular PREFERENCES: June, culture, outdoors, beaches, historic sites, wildlife ATTRACTION STYLE: Popular PACE: Medium 3 days in Maidenhead BY A USER FROM BELGIUM June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 2 days in Windsor BY A USER FROM UNITED KINGDOM August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 2 days in Berkshire BY A USER FROM UNITED STATES July, popular PREFERENCES: July ATTRACTION STYLE: Popular PACE: Medium 3 days in Ascot BY A USER FROM UNITED STATES June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 17 days in England BY A USER FROM CANADA May, culture, historic sites, museums, slow & easy, popular PREFERENCES: May, culture, historic sites, museums ATTRACTION STYLE: Popular PACE: Slow & easy 2 days in Berkshire BY A USER FROM UNITED STATES June, outdoors, romantic, historic sites, popular PREFERENCES: June, outdoors, romantic, historic sites ATTRACTION STYLE: Popular PACE: Medium 2 days in Berkshire BY A USER FROM UNITED STATES June, culture, outdoors, romantic, historic sites, museums, fast-paced, popular PREFERENCES: June, culture, outdoors, romantic, historic sites, museums ATTRACTION STYLE: Popular PACE: Fast-paced 1 day in Windsor BY A USER FROM UNITED KINGDOM June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 26 days in United Kingdom & Paris BY A USER FROM AUSTRALIA June, kids, popular PREFERENCES: June, kids ATTRACTION STYLE: Popular PACE: Medium 16 days in United Kingdom, Paris & Bordeaux BY A USER FROM AUSTRALIA June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium
View more plans