Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Maidenhead Vacations

Pack those stellar shades. We have Maidenhead vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Maidenhead – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Maidenhead vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Maidenhead

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Maidenhead vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Maidenhead well.

Top Hotel Deals

See all 1,114 Hotels in Maidenhead
Cliveden

Cliveden

Cliveden Estate, Maidenhead
    5.0 out of 5.0
     
     

    This family-friendly Maidenhead hotel is located near the airport, within 3 mi (5 km) of Cliveden House, Stanley Spencer Art Gallery and Maidenhead Railway Bridge. ...

    Cliveden$612

    Cliveden$612
    The Thames Hotel

    The Thames Hotel

    Ray Mead Road, Maidenhead
      3.0 out of 5.0
       
       

      Situated on a river, this hotel is 1.9 mi (3 km) from All Saints' Church and within 6 mi (10 km) of Eton College and Bray Marina. Cliveden House and Dorney Lake ...

      The Thames Hotel$95

      The Thames Hotel$95
      Thames Riviera Hotel

      Thames Riviera Hotel

      The Bridge, Maidenhead
        3.0 out of 5.0
         
         

        Situated in Maidenhead, this hotel is 1.7 mi (2.8 km) from All Saints' Church and 2.8 mi (4.5 km) from Bray Marina. Eton College and Cliveden House are also ...

        Thames Riviera Hotel$95

        Thames Riviera Hotel$95
        Fredrick's Hotel Restaurant & Spa

        Fredrick's Hotel Restaurant & Spa

        Shoppenhangers Road, Maidenhead
          4.0 out of 5.0
           
           

          Situated in Maidenhead, this luxury hotel is 1.2 mi (2 km) from All Saints' Church and 3.1 mi (4.9 km) from Bray Marina. Cliveden House and Bisham Abbey are ...

          Fredrick's Hotel Restaurant & Spa$118

          Fredrick's Hotel Restaurant & Spa$118
          The Crown

          The Crown

          The Moor, Maidenhead
            3.0 out of 5.0
             
             

            Situated in Cookham, this bed & breakfast is 0.1 mi (0.2 km) from Stanley Spencer Art Gallery and within 3 mi (5 km) of Cliveden House and Longridge Activity ...

            Holiday Inn Maidenhead Windsor

            Holiday Inn Maidenhead Windsor

            Manor Lane, Maidenhead
              4.0 out of 5.0
               
               

              Situated in Maidenhead, this hotel is 1.2 mi (2 km) from All Saints' Church and within 3 mi (5 km) of Maidenhead Railway Bridge and Bray Marina. Stanley Spencer ...

              Holiday Inn Maidenhead Windsor$57

              Holiday Inn Maidenhead Windsor$57
              Taplow House Hotel

              Taplow House Hotel

              Berry Hill, Maidenhead
                4.0 out of 5.0
                 
                 

                Situated in a rural location, this hotel is within 3 mi (5 km) of All Saints' Church, Cliveden House, and Bray Marina. Eton College and Dorney Lake are also ...

                Crazy Fox Hurley Boutique Bed & Breakfast

                Crazy Fox Hurley Boutique Bed & Breakfast

                High Street, Maidenhead
                  5.0 out of 5.0
                   
                   

                  Situated in Hurley, this luxury bed & breakfast is 1.6 mi (2.6 km) from Bisham Abbey and 2.8 mi (4.6 km) from Longridge Activity Centre. All Saints' Church and ...

                  Hurley House Hotel

                  Hurley House Hotel

                  Henley Road, Hurley, Berkshire, Maidenhead
                    4.0 out of 5.0
                     
                     

                    Situated in Maidenhead, this hotel is 2.6 mi (4.3 km) from Bisham Abbey and 2.9 mi (4.7 km) from All Saints' Church. Longridge Activity Centre and Leander Club ...

                    CIM Moor Hall Conference Centre

                    CIM Moor Hall Conference Centre

                    CIM Moor Hall, Maidenhead
                      3.5 out of 5.0
                       
                       

                      Situated on a river, this hotel is 0.2 mi (0.3 km) from Stanley Spencer Art Gallery and 2.4 mi (3.9 km) from Cliveden House. Windsor Castle is 9.9 mi (16 km) ...

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.